


Eye of the Storm

by hash_slinging_slasher



Category: Supernatural
Genre: AU, Alternate Universe - Real World, Angst, Attempted Rape/Non-Con, Conspiracy, Explicit Sexual Content, F/M, Forbidden Love, Human Ruby, M/M, New York City, Romance, Sexual Content, Shower Sex, Smut, Spies & Secret Agents
Language: English
Status: In-Progress
Published: 2014-05-02
Updated: 2015-10-27
Packaged: 2018-01-21 14:52:09
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 12
Words: 45,850
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1554275
Author URL: https://archiveofourown.org/users/hash_slinging_slasher/pseuds/hash_slinging_slasher
Summary: <blockquote class="userstuff">
              <p>Lilith, the campaign manager for Presidential candidate Mark Lucifer, hires Ruby to kidnap the competition's son. It's a job like any other; seduce a shallow guy, tie him up, hold him ransom for whatever high-profile entity he's attached to, and get home just in time to watch the new Game of Thrones and count up her reward money. But the one thing she was never prepared for was falling in love with her assignment.<br/>Sam Winchester hates being the son of a politician, and he hates his path in life even more. A reluctant law student at NYU with no time for anything else, his world is turned upside down when he meets the mysterious Ruby at a nightclub his brother dragged him to.<br/>In each other they find true freedom in the midst of radically different, yet equally lonely lives, but she knows their relationship is just a time bomb waiting to explode. How long can she hide the truth from Sam and deceive her short-tempered boss before she puts both her and Sam in more danger?</p>
            </blockquote>





	1. The Ruby in the Rough

**Author's Note:**

> This is PREDOMINANTLY a romantic Sam/Ruby fic with a pinch of Destiel. There are lots of smut scenes, so... yup. Additionally, there is a scene depicting, although not graphically, torture, gun fire, and threatened sexual assault. If you are triggered by these things, you can still read the fic, but I will tell you when you reach the chapter you should skip. A summary free of triggers will be found at the end of that chapter.
> 
> Please kudos and review!

_Do you hear the sound fallin' on this town?_

_We all know that it's the devil coming 'round_

_And when the devil's on your back_

_All you can do is turn and run_

_-[Eye of the Storm, Gareth Emery feat. Gavin Beach](https://www.youtube.com/watch?v=YkooqDy-2ww) (youtube link)_

 

Lilith Carter was an extremely busy woman. Between managing to walk in 4 inch pumps on a daily basis, and getting all her phone calls and emails done by promptly five o’clock every evening, she barely had enough time to make it to her Zumba class. Her life was her work.

As campaign manager for Mark Lucifer, one of the Republican contenders for the presidency, she felt that the fate of the United States rested squarely on her shoulders. And she took that responsibility very seriously. She had to ensure that the country was headed in the right direction, and she would stop at nothing to win him this primary, and eventually the presidency. Even if she had to get her hands dirty.

That was exactly why she set up a meeting with Ruby, this shady entity who wore nothing but black leather and refused to reveal her last name. If Lilith saw her on the street she would be disgusted, but every source assured her this girl was the best money could buy. Looking past Ruby’s poor fashion decisions, Lilith could see why. She was petite, slender, with pouty lips that would drive any man wild. And that was the weakness of men, at least the straight ones. Lilith knew that well.

"Ah, you’re here!" she began, seeing Ruby hovering in the doorway, looking unimpressed. She uncrossed her legs to rise out of her chair, and came to shake her hand, trying to seem as polite and hospitable as possible. Part of this job was hiding one’s true feelings, and she considered herself a pro.

Ruby shook her hand, but with a peculiar hesitancy, as if she already sensed the disgust that Lilith was hiding. She scanned the model-like figure of the woman; shiny red heels, tight pencil skirt and a blouse that left nothing to the imagination. Loose curls of blonde hair were the cherry on top of her look. Ruby wasn’t feeling so warm towards this woman either.

"Sit down, have a glass of water," Lilith said, gesturing to the chair in front of her desk, and a water cooler in the corner of the room. Ruby sat herself down, ignoring the invitation to have a drink, her expression of complete disinterest and apathy still firmly in place. Lilith wondered if Ruby had ever smiled in her life.

"So," she began once again, smiling brightly, resting her forearms on her desk. "Let’s cut right to the chase. I’ve been told by nearly all my advisors that you are one of the best, well- privately hired agents in the country, if that’s how you would describe your job."

"Thanks. I take pride in my work," Ruby responded sarcastically.

"Well… that’s good to hear! I’m sure my assistant has given you the general reason why you’re here, but let me just reiterate everything, how about that?"

Ruby motioned for her to continue.

She opened her MacBook in front of her and began typing away. When she found what she was looking for, she flipped it around to show Ruby what was on the screen.

"As you can see, Mr. Lucifer is not doing as well as we’d hoped in the latest opinion polls." She pointed to the bar graphs which indicated that Lucifer’s opponent John Winchester was favored by 54% of Republican voters. It wasn’t a drastic amount, but considering it was November, and the primaries began in January in some states, something had to be done.

"My team and I have come up with a strategy we think may help—or even eradicate—this gap, if all goes as planned. See, Mr. Winchester has two sons whom he cares about very much, and we think that if one of them were to be, say, detained?- he might reconsider whether or not the presidency is really what he wants in life."

Ruby shrugged.

"So you’re beating around the bush, you want me to hold them ransom."

Lilith interlaced her fingers and bit her lip.

"Actually, you’ll only be taking one of them. Sam." She passed a picture across her glass desk for Ruby to see. He was tall and muscular with rather long brown hair. Certainly not unattractive.

Lilith continued. “26, law student at NYU. Sources say he’s easily Mr. Winchester’s favorite, and besides, it’d be too risky to capture both considering what’s at stake here. Oh, and on that note-” she leaned in close and taking the hint, Ruby did too- “I hope it goes without saying that Mr. Lucifer and I are expecting very specific results. A slip up will not be tolerated by my colleagues and myself. Are we clear?”

Ruby nodded in understanding, still pretty disinterested. It amused Ruby hearing the implied threat in her tone; it was laughable that Lilith wanted to intimidate her.

"Now, to discuss the money matters- our final offer is $800,000 once the job is complete and Mr. Winchester has stepped down from the Republican nomination."

The girl in front of her crossed her arms, cocky and defiant.

"Make it a million. I’ve killed hobos for more."

Lilith forced a smile, trying to seem understanding, when in reality the only thing stopping her from smacking this god damn slut right across the face was the knowledge that there was a bigger picture here. Her job was simple, to make Mark Lucifer the 45th President of the United States, and she wasn’t going to let some grunge bitch get in the way of that, especially when said grunge bitch was vital to the operation.

"Unfortunately that is our final offer, we simply don’t have the budget-" Ruby stood and started making her way towards the door.

"But- I’m sure an adjustment can be arranged!" she called out, desperate for the girl to come back. She hated knowing how easily be manipulated by a greedy, leather clad, catwoman wannabe, but once again, she had to think of the bigger picture here.

"Sounds good," Ruby said as she sat down once again. "So, how am I supposed to get near him?"

Lilith copied something with a pristine golf pencil from her computer onto a slip of paper. She passed it to Ruby. It was an address.

"Sam and his brother frequent this club. Especially on Fridays, as it happens to be today. Get him drunk, get him to come home with you, whatever it takes. Then your work is practically done. He’s a man, it shouldn’t be hard.”

Ruby smirked. This was one of the few things she loved about her career. Her sexuality was something she prided herself on, and she adored being able to use it to manipulate shallow guys. The more they drank, the more their brain migrated South.

"And, uh… where am I supposed to deliver him?” she asked.

"Oh, yes, I almost forgot!" exclaimed Lilith. She slid another slip of paper over to the girl. “Here’s the address. It’s a property in upstate New York, an abandoned factory that Mr. Lucifer owns, but does not currently use. It’s a bit of a drive from the city but if you use Rohypnol on him, it should be enough to last.”

"Come again?"

"Roofies. Roofie him, sweetie."

Ruby nodded in understanding. She had a host of sedatives and date-rape drugs; that could certainly be arranged.

"Well I think that just about covers it. Anything else I can clarify?" Lilith asked cheerfully. In truth it was a genuine cheerfulness. Finally, this girl would be out of her office.

"I’m good," Ruby shrugged.

"Great! And let’s exchange numbers just to make sure we’re on the same page with how your assignment is going at all stages. Here you go!" She handed over yet another little slip of paper. Somehow she seemed to have an endless supply of those, Ruby thought to herself.

"I’ll text you," Ruby said blandly, in a tone of voice that made Lilith sure she wouldn't. She grabbed her purse from the floor and promptly left the office.

As the door closed, Lilith sighed in relief. She leaned back in her chair and ran her hands through voluminous blonde curls. The only upside to working with this girl was that Ruby hated her just as much as she hated Ruby.

She strolled towards the massive glass observation window on the other side of her office. It relaxed her to look across the parking lot and see rows of signs and bumper stickers exclaiming, “Choose Lucifer for ‘16!”

 _You work hard Lilith_ , she thought to herself.  _Mark Lucifer is lucky to have you._

………………………………………………………………………………………………………

Sam Winchester was in his room, relaxing on his bed and watching Game of Thrones on his laptop when his brother called. He had to pause the video just as the plot was getting interesting, so he was pretty annoyed.

"What?" he asked, trying to communicate to Dean that this was not a good time.

"It’s Friday, Sammy!" His brother was clearly already in the mood for celebration. He always was.

"Whaddaya say we hit up Lazer?" He was referring, of course, to his favorite club in New York, which he claimed had the hottest of both genders that the city had to offer. Sam tried to stay away from stereotyping, but his brother definitely wasn’t helping convince him that bisexuals  _weren’t_ total sluts.

"Look, I’m tired, Dad’s holding some stupid dinner party tomorrow with a senator from California who he wants to impress, and I’m supposed to be there. Plus I have a test on Monday, so that doesn’t leave much room for studying."

"Come on, pleeeeease?" He could practically see Dean’s signature pouty face. "Hey, who knows, you might get lucky too, huh Sammy?"

He sighed. He wasn’t big on trying to get girls at clubs, but… he certainly wasn’t opposed to it either.

"Ok, fine. But I am  _not_  letting another gay stripper do coke off your ass in the backseat of my car.”

"Yeah, sure, of course," Dean responded, but Sam doubted he even listened to what he said.

“Kay, well um… meet you there at 12.”

He hung up promptly and let his phone fall to the floor next to his bed. His head began to throb, and he decided that maybe it wasn’t the best idea to be watching Game of Thrones before he would be up all night attending a sleazy bar he didn’t even want to be at. Sam hadn’t realized it until now, but he was exhausted.

He set an alarm on his phone, and let himself drift into slumber.

………………………………………………………………………………………………………

Ruby detested her job, there was no doubt about it. All the sketchy people, all the empty alleys and warehouses, mostly the affiliations she was forced to have. One of the few perks was the money; by all standards, she was filthy rich.

As she lay lazily draped on her mauve leather couch, wearing nothing but her bra and panties, enjoying the latest episode of Game of Thrones, her phone alarm beeped. She groaned and hoisted herself up, forced to pause the TV just on Jaime Lannister, mid-sentence. It was 10 o’clock, and she had to start primping for her trip to Lazer.

She strolled from the living room into her bedroom, past numerous large windows with a view of the street. Ruby didn’t give a fuck if anyone saw her in her skimpy undergarments; if anything, the thought excited her.

With the push of a button, the automatic doors to her closet opened, revealing a long rack of fancy dresses. Ball gowns, short skimpy little things, satin, lace, sequins. The works.

She took a good 5 minutes looking through her wardrobe, selecting a piece. She didn’t want to draw attention to herself by being too flashy, so she quickly eliminated the ones with loud fur and sequins; those were pretty much exclusively reserved for her masquerades as a hooker on a street corner when her bosses wanted to target sleazy senators. It couldn’t be too plain either; this was a pretty happening night club. She ended up deciding on a body-hugging black dress, selecting shiny nude pumps and earrings made of a long string of intertwined gold hoops to accompany it. The weather had been nice that day, but it was November in New York, so she grabbed an elegant red jacket to go with her outfit. She grinned as she held her selections against her body, admiring herself in the mirror. The ensemble was perfect. Classy, elegant, not too flashy, but it still flaunted every sensual curve of her body.

When it came to make up, she went with a rather simple look; red lips, smoky, purple-tinted eye shadow, and a touch of dark pink blush. She realized too late that soft ringlets she curled her hair into reminded her of Lilith, but it gave her satisfaction knowing they looked much better on her.

Midnight seemed like a pretty reasonable target for when to arrive.She left her apartment and took the elevator to the ground floor, ready to hail a cab and get into character for her assignment. Just a run of the mill kidnapping, a night like any other. And once she was done, she could finally get back home to finish Game of Thrones.

………………………………………………………………………………………………………

Sam found himself surprisingly more excited than he’d thought he would be for this night on the town with his brother. Dean was kind of right; he wouldn’t mind meeting someone. He put on a nice black button-up shirt and jeans, straddling the line between sloppy and just tastefully casual, and he was on his way.

When he arrived, he stood on the sidewalk and looked up at the spectacle of a building. He was practically blinded by neon signs everywhere, both girls and guys in tight clothes giving him winks as they passed by, the thick fog of smoke in the air.

Sam couldn’t see a thing once he entered the club. The smell of musky perfume and sweat was unavoidable as he tried to squirm through the sea of people and locate his brother. His height made him stick out like a sore thumb, and yet it was of no help in finding Dean. It was no use, and quite honestly he wasn’t sure why he’d bothered looking. The priority then was to find a place to sit down and  _breathe._

When he finally made it to the bar at the other end of the club and hopped onto one of the stools, he pulled out his phone to call Dean. Unfortunately,  he couldn’t hear anything over the bass-heavy music blasting from every corner of the building. He sighed, letting his head fall into the palms of his hands in exhaustion.

"Hey, you ok there?"

Out of the blue, out of the ocean of deafening drum beats and screams and pounding feet, emerged a single, sweet voice.

Sam looked up. A girl stood next to him, leaning against the bar casually, her dark brown ringlets cascading across her shoulders.

"Yeah, I’m ok," he chuckled. "I don’t usually go to places like this."

"Neither do I," she sighed. "But I thought it might be fun to meet guys, have some fun, ya know?" She sat herself down next to him, and got the attention of the bartender.

"I’m Ruby," she smiled and he found himself really seeing her face for the first time. He would say she was beautiful, but so many girls were. Something else, something intangible drew him to her.

"Sam," he replied, and they shook hands. Just then the bartender arrived. The woman had an extremely complex hairdo, and sharply penciled eyebrows. Sam saw Ruby’s quick glance away from the woman’s head, the small smile she flashed him agreeing with the slightly awestruck look on his face. Someone needed to tone down the hairspray.

"Margarita, rocks, no salt," Ruby told her, and motioned for Sam to place his order.

"Scotch for me."

Sam wasn’t shy, he liked people, he just had no idea how to get a conversation going. He simply smiled at Ruby again, admiring the way her nude pumps accentuated her legs. She sensed his awkwardness and made a clear effort to reignite the conversation.

"I’m- sorry if I’m being too forward," she confessed. "But I guess… so many people everywhere, and there’s this cute guy, sitting alone at the bar, away from all of it, set apart from this mob. I had to know that handsome stranger’s name."

Sam blushed as if he’d never received a compliment in his life. The thing was, Ruby wasn’t even trying that hard. He did stand out, and he was a sweet guy, she could tell.

Their drinks came and they each took a long sip.

"So, Ruby," he began, coughing a little as the alcohol burned its way down his throat. “What do you do?”

Ruby sighed, realizing she’d seldom been asked that question. Usually her job was to nudge the guy into spilling his life story, get him drunk as hell, and back to her apartment. A gentleman would take more skill.

"Not much right now," she shrugged and took another delicate sip. Her pouty lips left a smudge of red lipstick on the side of the glass- kinda sexy, Sam thought. “In between jobs I guess. You?”

"Law student at NYU."

She sensed he hated saying those words for some reason. Lilith acted like he’d be bragging about it, and that he was John Winchester’s son, but not a peep.

"How’s that?" she asked, curious. She leaned in a little closer, trying to be more seductive. Sam took a drawn out swig, maybe trying to distract himself.

"It’s good. I mean- not fun, but it’s useful information. I’m not really sure what I want to do with it, but my Dad wants me to become a politician."

"Is that what you want?"

"Not really."

"Well, that’s parents for you." She remarked, and let her eyes drift up to look right into his. They were gorgeous. Hazel with a ring of green on the outside and gold around his pupil, like a sunflower. His eyes beautifully complimented hid big goofy smile, lighting up his face. Ruby had completely forgotten that she was supposed to be acting.

"You look- really beautiful tonight," he said, sweet and low, making her blush.

"Thank you," she responded, genuinely flattered. She looked down at her dress and realized it wasn’t even hugging her body the way she had arranged it before coming here.

"You’re one to talk!" Her eyes scanned his body. "I like a man in jeans."

He chuckled as if he couldn’t believe she was complementing his poor attempt at semi-formal.

Ruby leaned in even closer, and looked up at him with full brown eyes, framed by long and defined lashes.

She whispered sensually, “Like ‘em even better without.”

Internally, Ruby cringed at her own poor attempt at a pickup line. Fuck, she had probably completely weirded him out. Then again, in an hour or two, he’d be roofied and tied up in the trunk of her car. His attraction to her was of minor consequence.

"Wow," he responded, amused, raising his eyebrows. He would humor her. Ruby seemed very upfront, and he liked that in a girl. And truthfully, she had just vocalized what he wanted to—but couldn’t—say. Despite having only known her for something like 20 minutes, he could totally picture her screaming his name, tangled in sheets. He had to stop thinking about it though; put a cap on that thought and save it for later.

Suddenly, he felt his phone vibrating erratically in his pocket, playing the Game of Thrones theme song.

"Dean? Where the hell are you?" He had to yell into the phone, and on top of that, his voice made it pretty evident he was beyond exasperated with his free-wheeling brother.

"Not good, Sammy," Dean responded, not even answering the question, before Sam heard him hurl into what sounded like a toilet. The echo indicated he was in the bathroom.

"Are you in the bathroom?" Sam shouted again, but Dean hung up.

"Ugh, fuck…" he sighed, embarrassed and disappointed that instead of driving home this beautiful and mysterious girl, he’d get Dean and the plastic bag he’d be puking into.

"I’m so sorry, it’s just that my brother-"

"No need to explain," Ruby interrupted him, giggling a bit. "So, you watch Game of Thrones?"

Sam’s eyes lit up.

"Oh yeah! I’m only on season 2 so- no spoilers!" He joked, and she mimed herself zipping her lips.

"So um… let me give you my number," Sam said as he pulled a napkin from the dispenser next to them, scribbled onto it neatly, and handed it to her.

"I’ll call you," she smiled. He walked away backwards so he could still see her, waving his arm casually as a way of saying goodbye, until he was forced to dive into the sea of people once again.

Looking at the napkin in her hand, Ruby thought about all the stupid slips of paper Lilith was always sliding her. It was an impersonal action for that horrid woman, a representation of her attitude towards Ruby. Hardly endearing.  _Here’s the information, now use it._ Sam was oddly cute when he was transcribing his number onto the difficult surface of the napkin; his tongue stuck out a little, he gripped the pen tightly. When he gave it to her, their skin grazed a bit, and his eyes sparkled like it was something precious.

She folded it up neatly and stuck it in her bra. It was precious.


	2. Change of Plan

During the cab ride back to her apartment, Ruby figured she should probably make an effort to contact Lilith to tell her things didn't go quite as planned. She freed her aching feet from the nude heels and exhaled slowly. Her eyes closed and she allowed her thoughts to mindlessly wander to the handsome man she had a drink with. She could vividly picture his big sunflower eyes, and his lips, and that strong jaw, perfect for kissing, or sitting on... Ruby snapped out of it when she remembered that her job wasn't to get all hot and bothered over her assignment.

She pulled out her phone and dialed up her loathsome boss, who picked up almost immediately.

"Hello, Lilith Carter speaking."

Just the sound of that superficial, saccharine voice made her want to rip her eardrums out. She didn't feel that she owed the woman any respect.

"Wow, what a shocker. Thanks for letting me know," Ruby began, sassy but coolly so.

Lilith, collected as ever, ignored the sarcastic remark.

"Have you got him?"

"Not yet," Ruby responded. "He had to leave early with his brother. I think he wanted to come home with me, but it ended there."

She heard the woman on the other end sigh, as if attempting to release her exasperation from her body.

"Alright, well I assume you have is number?

"Mhmm."

"Call him tomorrow like he's all you can think about," she said coolly, with a breathy voice that was meant to be mockingly sultry. "Like you can't even handle how much you want to fuck him."

That wasn't far from the truth, Ruby thought to herself.

"Sounds good," she affirmed apathetically, and hung up before she could hear another word from that little blonde bitch's mouth.

...

The guttural, wrenching noises coming from the backseat had Sam wanting to jump out of the car. Sometimes Dean tried to speak up and apologize for the inconvenience he'd caused his brother, but ended up interrupting himself as he threw up into his plastic bag. Sam could see it from his rearview mirror, so he turned it to the side. An accident didn't sound so bad at this point.

"I'm- sorry, man," Dean said with difficulty, as he tried to hold his churning stomach, and speak through the haze of alcohol. "Come on though, you don't even like night clu-" He vomited into the bag once again.

Sam sighed. Should he tell Dean about Ruby? His brother would just tease him, but at least he could make him finally feel guilty for being 30 and needing a chaperone just to get smashed at bars.

"I met someone."

"Ah, that's my boy Sammy!" Dean reached from the backseat to pat Sam heartily on the shoulder, but Sam pushed his sweaty hand away. "You should've taken her home!"

Sam groaned as his capability to tolerate the sheer stupidity of Dean's drunken logic was running out. The last thing on earth he wanted was to see Ruby, her beautiful clothes and her sultry invitation to take him home, cooped up in the backseat with this intoxicated mess. If having to sit right next to Dean puking into a clear plastic bag wasn't the biggest boner killer of all time, he didn't know what was.

"Yeah Dean, who wouldn't be in the mood for hooking up after a long car ride with you?"

His brother didn't say anything, and Sam didn't even hear any disgusting sounds in response. He pulled over and saw him, passed out, the container of his vomit spilled all over the floor.

Sam shouted profanities shamelessly as he got out of the driver's seat and opened to door to the back. He flipped Dean over onto his stomach and tried his best to ignore the disgusting puddle on the floor of his luxury car. Man, he never would've let that happen in his precious Impala, Sam thought to himself.

After a miserable and completely revolting 20 minutes, he reached his apartment. It was probably best that Dean stayed the night, and that way Sam could definitely force him to clean up the mess in the backseat. He hoisted Dean into his arms with difficulty, considering his brother didn't weigh much less than he did, and managed to push open the door to the lobby with his leg. The guy at the front desk gave him a suspicious look, probably wondering if this was some kind of date rape situation. Sam sensed that too.

"My brother," he chuckled, realizing that probably still wouldn't convince him. "Took him to a club, big mistake."

When he reached his floor by elevator, he released Dean, as gently as he could manage, onto the carpeted floor in front of his door. He leaned his head against the wall and exhaled deeply. He thought about Ruby, and how much he wished he was carrying her into his apartment, kissing her against pressed against the wall of his bedroom, and watching her little black dress fall to her ankles. He imagined with much certainty that she was even more gorgeous naked.

He reluctantly paused his thoughts, forced to focus on the situation at hand. With much effort, he dragged Dean in and dumped him on his couch, face down, unenthusiastic to even throw a blanket over him or take his shoes off. Sam was too exhausted to care if Dean blew chunks all over his floor.

Just as he was getting into bed, he remembered the disgusting spill in his backseat. Unfortunately, he'd have to at least clean it out adequately to make sure it didn't stink up his car. He grabbed a bucket, dish soap, and a sponge from a closet, and made his way to the parking garage in pajamas and flip flops. It would be a long night.

..........................................................................................................................................

Sam decided to take the day off from classes that morning. He was pretty disoriented and beginning to get another headache- those were becoming increasingly common for some reason. More importantly, he knew he'd be praying constantly for Ruby to call him. He wished she'd given him her number too, so he wouldn't be so impatiently waiting.

He wondered if she'd even bother at all. Maybe she was just being polite, pretending to listen to him and seem interested, and maybe she went home with someone else after he left. Sam felt an unnatural surge of jealousy even at the thought of some hotter, more suave guy scooping up Ruby and taking her home, when it could've been him.

At at 10:57 am, when he was still groggy and splayed out on his bed, his phone buzzed. He jumped up to answer. There was no caller ID, so his hopes were up.

"Hello?" he answered, trying to sound collected. His heart pounded and his ears anticipated the voice of the girl he met last night.

"Sam? Hi, it's Ruby!"

He smiled childishly when he received what he considered proof that she did, in fact, like him.

"Yeah, it's me," he said, suddenly aware of his voice. "How are you?"

She chuckled lightly, and sighed.

"Good, yeah," she paused, and lowered her voice. "I couldn't stop thinking about you."

Ruby was so sexy, even over the phone. Sam could picture her casual smile, and her twirling her hair around her finger. He didn't want to be too hasty, but all he knew was that he really wanted to see her again, in a more private environment, to get to know her more.

"I was wondering if you wanted to maybe go to lunch sometime? I know it's last minute, but uh... I'm free today actually, and I know a nice cafe that's not usually too crowded."

"Sounds great," she responded, excitement bubbling in her voice. Sam found himself grinning even wider, pressing the phone closer to his ear.

"Which one?" she asked.

"It's on Ennis street, I'm forgetting the name..."

"Drizzle?" he suggested.

"Yeah, that's it!" Ruby replied.

"So... how does 12:30 sound?"

............................................................................................................................................................

Ruby strolled into Drizzle a bit late, but she had good reason. She had gotten lazy one day the previous week and bought some discount pet food for her cat, a pompous little tabby named Meg. In retrospect it was a stupid decision, as she awoke that morning smelling something odd, and seeing her pet lying next to her, looking somewhat guilty. Meg had thrown up all over her newly installed rug, and despite having spent her morning tirelessly scrubbing at it, Ruby was still unsuccessful in removing the brown-tinted stain. She barely had time to put together a decent outfit.

The cafe wasn't large, and she locked eyes with her date very quickly. He looked more casual than he had last night, but his hair was much neater. He was staring intently at his phone, probably waiting for a text, as his other hand maintained a loose grasp on his coffee.

Ruby approached the table coolly, smiling, and lifting her Fendi sunglasses up to rest them on her hair like a headband. She placed her arms on the table, fingers splayed out, as Sam looked up.

"Hey," he said as she sat herself down opposite him. "So um, how was your morning?"

Ruby rolled her eyes and sighed.

"Not to harsh your mood, but... terrible. My cat puked all over my new rug, and I was late because I had to clean it up."

Sam instantly started laughing to himself. Ruby was a bit confused with his amused response to her misfortune, and looked at him, puzzled, and his chuckles died down.

"Oh, sorry! It's just that my brother threw up in the back of my car last night and I had to stay up til 3am cleaning it. So I feel your pain."

Ruby giggled once she understood. It struck her then how odd it was that their lives so paralleled each other; the both watch Game of Thrones, they knew this cafe, the irresponsible annoyances in their care tossed their cookies.

She hardly noticed when a waiter approached their table. He was a bony, cheerful looking man with short brown hair and disproportionately pronounced ears. His name tag read Garth.

"Are you ready to order, ma'am?"

Ruby hadn't taken time to look at the menu, but she hardly needed to. She had grown a particular taste over her years in New York for the delectable apricot pastry that only the Drizzle cafe offered.

"I'll have the apricot pastry, and some iced tea." She smiled and handed Garth the menu, and he shuffled off.

Ruby turned to Sam once again. His sunflower eyes were different in this light, a little more greenish, still beautiful. She almost looked upon him like a child; he showed emotion so genuinely in a way Ruby had never quite been able to.

Sam spoke up, ending the brief silence.

"The pastries here are pretty good, but nothing beats the ones at a place near where I grew up."

"And where's that?" she asked, intrigued.

"Lawrence, Kansas," he answered. "Doesn't sound like much of a place, I know, but it's a nice town. I guess I always kind of wanted to see what more excited places have to offer, that's why I moved to the city."

Ruby was listening intently, genuinely interested, until her eyes caught a glimpse of the last thing on earth she wanted to see; ridiculously large Gucci sunglasses, red lips, and worst of all, barrel curls of blonde hair. The fact that Lilith found her wasn't surprising, but it was creepy nonetheless. When Ruby did a job, she did it her way, and she didn't want her boss snooping around. Still, this was one million dollars. She decided she would cooperate.

Sam noticed her staring into the space behind him, and flipped around to see what it is she was focused on.

"What is it?"

"Oh, um- just the artwork here, it's very nice," Ruby chuckled.

Garth returned with a clear glass of ice tea, lemon neatly wedged onto the rim, and a small plate with the apricot pastry. He laid her food down on the table, and smiled politely when Ruby thanked him.

"So," she began, initiating conversation. "Winchester... any relation to John Winchester?" She wanted to look like she was joking, making small talk, wondering if he would actually reveal the truth.

Sam thought to himself- she wouldn't judge him, or be interested in him only for his semi-celebrity status, would she? He raised his eyebrows, and opened his mouth to speak, but hesitated. Then he made up his mind to tell her.

"Actually... he's my father."

Ruby pretended to look shocked, in an amused way.

"Wow, really? I was mostly kidding but... wow. What's that like?"

Ruby really did want to know; she wanted to know what it was like, having that connection to such a prominent politician, that kind of pressure. It didn't seem like he did, considering his doubt over whether or not he should tell her.

Sam shrugged, and she took the hint that he didn't want to talk about it. She changed the subject and asked him about Dean, leading Sam to a lengthy rant about his irresponsible hazard of a brother, and how their family was always so tense because of his father's ridiculous expectations for him. Dean came out a couple months after a long road trip with a high school buddy, whom he had developed unrequited feelings for. Sam remembered when Dean called him up and asked him to come over to talk through his confusion. And when he decided to tell his father, it didn't go very well. John wasn't terribly homophobic, in a general sense, but the thought of his son being attracted to men as well as women had clearly made him uncomfortable. Eventually he came to an indifferent acceptance, but he would do anything to steer the conversation away from Dean's sexuality, or Dean at all.

As Sam finished his story, Ruby spied Lilith motioning for her to steer the conversation back to her, and getting him home.

She placed a tender hand to his cheek, feeling the warmth of his smooth skin. He smiled sensitively when she looked into his eyes.

"I get it," she said softly, and rose up a bit, with pouting lips that truly longed for the feel of his. Sam was a bit surprised when she kissed him, but he responded gently and moved his hand up to caress her neck, and deepen it. Ruby allowed herself to release, just for the moment, from her masquerade under Lilith; to give in to the ignorant bliss of the feeling that she was really on a date, and really with this man.

Suddenly, Ruby felt a rush of cold spill onto her lap. She jumped back, startled, and noticed the source of the sudden discomfort. On the table lay her iced tea, tipped onto its side, spilling the pale liquid across the entire surface. Little rivulets dripped down the sides and fell to the floor.

"Oh my gosh, I'm so, so sorry!" Sam exclaimed.

He looked utterly mortified. Ruby's jeans were covered in streams and splashes of tea, all because he was such a clumsy kisser as to knock it over with his elbow. He quickly grabbed a few napkins from the dispenser nearby, as if he was going to give dry her head to toe, and somehow not come off as a perv.

Ruby giggled, assuring him she wasn't all that upset. He awkwardly handed her the napkins, and she pressed them against the wet fabric, trying to dry it, but without much luck.

"Don't worry, I was being pretty impulsive there. I didn't mean to freak you out," she assured him. The bright scarlet of his cheeks died down a bit, but he still held his embarrassed half-smile.

"No, it was... really nice, actually," he confessed.

The pretentious blonde was still several tables away, looked oddly pleased. Ruby wondered if Lilith thought that she had orchestrated the whole thing, intentionally startling Sam, making him feel guilty for the accident. In truth Ruby felt bad for him. He looked so ashamed, self-conscious even.

"I can make it up to you- I'll get the tab, and if you maybe want to go have dinner sometime... it would be on me." He grinned, hoping his invitation to a more formal date wasn't out of place, but very happy that he gotten the courage to ask her.

"I'd love that," she said simply, sweetly, and stood on her toes to press another chaste kiss to his lips.

When their table and chairs were clean, the sat down again. Sam placed his forearms on the table, so his hands were close to hers, and spoke to her with such sincerity it broke her heart.

"I know exactly which place. The food's great, the environments really nice. It's one of my favorites. But it'll be a surprise."

Sam smiled to himself, picturing vividly the first meal he'd ever had in New York, at that restaurant, with his dad and brother. It was one of the few times in the last several years they were able to spend quality time together, and actually get along, rather than letting some argument get blown out of proportion, as it often did. And when it often did, it was Sam and John. Beyond that, it was the beginning of a new chapter for him, one he hardly chose to begin, but he was making the best of it. Since having to leave Stanford his family had, naturally, been more sensitive to his emotional needs. In a sense it was his ultimate happy place, and to take this beautiful woman there would only add to the book of fond memories.

"How mysterious," Ruby responded, with a flirtatious lift of her eyebrows. "Just going to whisk me away?"

"No, I mean- not when you say it like that..."

Ruby chuckled softly, and assuring him it was a remark in jest, she took his hand into both of hers.

"You're such a gentleman," she said as she traced the strong ridges veins of his fingers affectionately. "Whisk me away any day."

And he already had, from the moment she looked into his vibrant sunflower eyes.

Sam broke away to pull out his phone, presumably to schedule their dinner date. Ruby, head in the gutter as always, thought smugly to herself that he had better leave the following morning open too. Unfortunately, her conscience had to step in eventually and remind her that she had nothing to be excited for, beyond seeing him struggle and fall unconscious as she violently kidnaps him and throws him in a warehouse to be tortured.

Ruby looked over Sam's shoulder as he searched through his calendar, and noticed Lilith was gone. She was relieved, but hit with a sharp pang of sorrow now that she truly understood what an awful job she had been employed to do. What was a million dollars when this sweet, innocent man would suffer horribly, and have his heart ripped out of his chest? Gosh, the way he was falling for her, he'd probably never date again, if he even made it out of this alive.

"So, next Saturday the 11th I'm available..."

"Perfect." Ruby's schedule was wide open, truth be told. It was a lonely life to lead, no friends, few affiliations beyond the sketchy ones she tried desperately to leave in her past, but it sure paid.

"Great," he smiled, hiding his giddiness, as he typed away at the screen of his phone. "8 o'clock? I'll pick you up."

There was no way Lilith would be ok with him seeing her apartment. It would sell her out in an instant if Sam managed to tell the police her whereabouts once the cat was out of the bag.

"Oh don't worry about it, I'll just take a cab to your place. Mine's a mess, it's pretty embarrassing," Ruby lied, but she wasn't really doing anything shady. She wasn't going to take a cab though, she'd take her car, park it close enough so she could throw him in there that night, and not raise any eyebrows.

"Ok. Just gonna text you my address..." Sam went to his phone once again, and tapped away, with his tongue sticking out to the side a bit, the same face he made when he scribbled his phone number on a napkin for her.

"Alright. Sent."

Ruby felt her phone buzz in her purse.

They flagged the waiter to get the check, and after Sam paid, she watched him start to put his belongings back into his briefcase, and his jean jacket over his torso.

"Hey, I'm sorry, but I should probably at least make it to my afternoon classes," he explained. "Political science and stuff, pretty boring but... I can't miss too much, or my Dad will go crazy."

"No worries," Ruby assured, beginning to assemble her things too, to be polite. She didn't want him to feel like he was disappointing her. He boldly swooped in and captured her lips for their third time, making Ruby weak at the knees in a way she'd only heard clichés describe. The simplicity of the gesture was the most romantic part of it for her; like something of a teaser trailer for what would come, she hoped.

Sam broke away and waved at her as he made his way out the door, and into the chaotic blur of people on the New York sidewalks. She tried to follow him with her eyes even as he turned away, until the crowd swallowed him, and she found herself truly alone.

Considering the life she lived, she'd led herself to believe she was impervious to loneliness. She didn't depend on anyone, she chose no companions but her cat, and she was perfectly comfortable in that. The loneliness she found herself unable to fight as she watched Sam Winchester's thick brown hair disappear was one she'd never felt; in a city of 8 million, there was only one she missed.

**Notes for the Chapter:**

> Hope you enjoyed this installment! Please please please kudos and comment if you enjoyed!
> 
> If you're on tumblr, and would like to sign up to help me edit this fic as I write it, message me @ burningruby.tumblr.com. Thank you!


	3. Special Request

**Notes for the Chapter:**

> Please kudos, comment and subscribe! :)  
> If you would like to join my team of editors, message me @ burningruby.tumblr.com. You'll get to see rough drafts of chapters before they're posted!  
> To get updates, track #eots sr (like Eye of the Storm Sam Ruby) on tumblr.  
> Enjoy!

Ruby made a point of going to the gym every Monday. It was a good way to start the week, and get her endorphins up to keep herself at least moderately happy. She donned nothing but a tight pink sports bra and yoga pants that cut of mid-thigh (lulu lemon had been having a sale last week, and she had taken full advantage.)

In a smaller room adjacent to the main one with all the machines, there was a nice carpeted area with yoga mats, exercise balls, anything else appropriate for quiet stretching.

Ruby always started there, stretching, winking at any sweaty guys in muscle shirts who passed by. As her legs stretched out as far as they could to the side, she spied a man with ruffled blonde hair smile at her. She smiled back, but wondered why she didn’t get as much of a thrill out of her subtle flirtation as she usually did; truth be told, of course she knew why.

When Ruby was ready, she scribbled a fake name (Daenerys; its not like anyone read those) on the whiteboard to claim a designated cross-trainer, and  
hopped on it. No trip to the gym was complete without her expensive pink earbuds, boasting impeccable sound quality, and some upbeat hip hop to drown out everything else. She popped the squishy ends in, and let the pounding of the bass fill her ears as her legs cycled to the rhythm. Her focus was on nothing but the rigorous work out; her eyes fell shut, her breathing was harsh but controlled: in through her nose, out through her mouth.

Several minutes into her time on the cross-trainer, her phone buzzed. Something told her it was Sam, or maybe that was just wishful thinking on her part. With her index finger, she firmly pressed to button to slow the machine to a stop, so she could see what it was.

Her face lit up when she saw Sam’s name on her screen.

In the message was nothing but a youtube link to a video of a guilty looking kitten with a dead bird lying before it, and an accompanying message.

_I saw this on facebook and thought of you ;)_

She tapped away in reply.

_Haha, thanks! But that cat looks nothing like Meg. Probably still smarter than she is._

I didn’t take long for him to reply either.

_She can’t be that bad, can she?_

Ruby chuckled to herself. She would’ve thrown the little bitch out years ago if she hadn’t been so attached to her pet. She often came home from a night of partying to find Meg viciously clawing at the carpet, and upon seeing her owner arrive, quickly shuffling to greet her as if Ruby hadn’t noticed her misbehavior.

She lost track of time texting Sam. Their conversation went as effortlessly at it did in person. From cats they moved on to experiences at the zoo, and from there to favorite ice cream, somehow winding up arguing over which Marvel character was the best. Ruby was naturally a fan of Natasha, but Sam liked Steve for his backstory.

Ruby was shaken by a light tap at her arm by an older woman in a loose tee shirt. She pulled out an earbud and the woman asked if Ruby was even using the cross-trainer. It occurred to her that she was hardly in the mood for exercise anymore. She would be perfectly happy sitting alone at home, with Meg purring in her lap, rapidly exchanging texts with Sam.

She gave up the machine, and never taking her eyes off her phone, made her way to the locker room.

……

Wednesday afternoon, Sam was in a class on judicial history that normally interested him, but his mind was completely elsewhere, buried in the small handheld screen he hid behind his laptop. It seemed he couldn’t go two minutes without texting Ruby, and about the silliest things. Cat memes became something of an inside joke; Sam spent a good ten minutes complaining about the bitter Professor Crowley, head of the law school, who seemed to hate even the most prestigious grad students he admitted.

And sometimes their messages got pretty flirty.

The phone buzzed in Sam’s lap for the millionth time that day, and he looked at the message the moment he felt the first shock of vibration.

_I really like tall guys. And you’re so buff too… are you a law student or a body builder?_

A pause, and then she added, _Pretty big hands too..._

He almost burst into laughter. Ruby was about as subtle as a giant Las Vegas billboard flashing “I’M HORNY!” in neon letters.

 _Haha, come on,_ he responded playfully. He quickly saw that Ruby was typing.

_All I can say is, I hope we get to see a little more of each other on Saturday night. ;)_

Ok, he was definitely getting laid. And he was on the verge of getting a hard on in the middle of a lecture if she didn’t stop teasing him. He could practically hear her sultry voice reading her words aloud, or whispering them in hot breath against his cheek, below his ear.

You can count on it, he texted her.

After his affirmation she didn’t respond for a little while. Sam found himself disappointed, but understood that it wasn’t like Ruby didn’t have a life outside flirting with the guy she met at a nightclub a week ago. He wished he could run all around New York just to find her place, swoop in and have her in his arms; take her then and there on a bed, on the floor, wherever she wanted. The thought of seeing her moaning in pleasure under him sent shivers down his spine.

Saturday couldn’t come soon enough.

……

Ruby had never been a morning person, but the occasional brightly colored dawn accompanied by cheerful bird chirps got her waking up on the right side of the bed.

Saturday, December 11th, was one of those rare occasions.

Her date would only be the finale of her day. She had agreed to do a pretty straightforward deal for 10 grand bugging some Sheriff Jody Mills in Brooklyn, but that would be a walk in the park. And much to her dread, she had agreed to have a conference call with both Senator Lucifer and Lilith, since this was going to be the day. The arrangements needed to be made so that everything went smoothly and according to plan.

After grabbing a very necessary mocha from Starbucks on her way to her day’s assignment, she took a cab to an out of the way parking garage where her client kept a car used for these types of missions; as far as Ruby knew, the license plate was registered to some old woman from Albany who died ten years ago. It showed, being that it was a mid-80s model Honda which didn’t appear to have been to the carwash since that decade. She found herself more worried about being seen driving the hideous conglomeration of rust and chipping paint than being caught committing a highly illegal crime. Ruby was so skilled, the thought seldom crossed her mind.

All that was done by noon, leaving a good two hours to kick back before having to call in to her dreaded bosses. The thought didn’t bug her as much as it previously had. She was fucking Sam Winchester tonight. The thought alone brought a smug grin to her face, one that would surely allow her to pull through the drudgery that  
awaited her.

At 2 o’clock sharp, she dialed Lilith’s office phone, and swallowed her pride in preparation. The familiar voice answered, predictably, “Lilith Carter speaking.”

Ruby groaned.

“Damn it, I was looking for a phone sex agency.”

“Stating one's name is a formality,” Lilith responded firmly, defending herself against Ruby’s insulting sarcasm.

“So, I’m finally meeting the infamous Ruby!” interjected a charismatic yet intimidating male voice she assumed belonged to Mark Lucifer himself.

“Don’t flatter me,” she spat back, her dry sense of humor as strong as ever.

“Well Missy, tonight’s the night, huh? You ready to put on an Oscar-winning performance?”

“I’m a privately hired agent. Go call Meryl Streep if you’re looking to wow the academy.”

It had been hardly 30 seconds, and her disgust for the senator had already eclipsed that she harbored for his campaign manager. It wasn’t just the patronizing way he spoke to her, like she was some naive little girl who existed only to be his pawn. He needed her. She wasn’t going to turn down a million dollars, but her political support was far from favoring Mark Lucifer. A man who needed to resort to kidnapping and holding ransom just to win the primaries was not one she wanted at the White House.

“Fair point. Luckily, from what I’ve heard, it doesn’t take much acting skill for you to play a desperate little slut, hmm?” he mocked her.

“Are we done here?” Ruby snapped back, unwilling to let the senator get the upper hand. He could call her every misogynistic insult in the book, she’d heard ‘em all before, and then some.

“3 am. Warehouse upstate. Simple as that,” he said in a voice that seemed plain, but was rich with underlying threat.

Ruby rolled her eyes. She always had the final word.

“Fantastic. Now you two can get back to fucking all over the American flag.” Swiftly, she hung up.

……………………………………

It was 7:50, only several minutes before Ruby would arrive. Sam took a deep breath, letting it fill his lungs completely, before exhaling in a drawn out, steady  
stream of air. He shouldn’t have been this nervous for a simple dinner date. His eyes had remained fixated on the mirror for the last 15 minutes, not questioning his  
physical appearance, but more because this dinner was a lot more significant for him than Ruby realized.

Looking intently at the face of the man before him, he noted the strange passage of time. His growing hair, pushed back neatly, was once shaggy and disheveled; his hollowed cheeks used to be a little pudgier. Deep down he still felt like he was 22, and at the same time, so much older.

While Jess would forever be 22.

Sam sighed and let his head fall, with his arms still outstretched against the bathroom counter. He had to tell Ruby. Before they slept together, before he really started getting attached, and until he didn’t have to look in the mirror anymore and see a damaged man.

His grim thoughts were interrupted by the bright ring of the doorbell. He felt his heart practically stop in his chest. Still, he smiled with excitement and opened the door, taking in the gorgeous woman standing before him.

Ruby smiled humbly when she saw how happy Sam was to see her. He motioned for her to step inside, still rendered speechless. Her dark hair hung in loose waves, her lips were painted a sexy deep red, and her dark blue dress hugged all her curves.

“You look so beautiful,” he said softly as he leaned in for a kiss. She draped her arms around his neck, letting their lips meet for just long enough for him to want to kiss her more passionately, but gently pulling away.

“Let’s save the rest for later,” she said, and took him by the hand.

………….

The drive to Sam’s secretly planned destination wasn’t too long. Ruby did nothing but stare out her window, watching the brightly lit shops and restaurants pass by in a blur, wondering to herself if she even knew where she was being taken.

She never would’ve guessed it was a rowdy bar.

He pulled the car into a small parking lot right in front of the restaurant, a rustic but clearly happening place that read, “The Roadhouse.” Suffice to say, this wasn’t what she was expecting.

Sam chuckled when he saw her mild surprise.

“Ok, I know what you’re thinking, but it’s actually pretty classy, I promise!”

“Don’t worry, I believe you!” Ruby assured him, giggling herself. She would give him the benefit of the doubt.

She was pleasantly surprised. It immediately struck Ruby as a friendly, jovial atmosphere. At the tables sat old men sharing a beer, young men flirting with the slim blonde bartender, even other couples looking lovingly at each other.

“Hey Jo!” Sam leaned against the bar and addressed the blonde Ruby had noticed as she walked in.

The woman handed out the last of the drinks she was preparing and made her way to the other end of the bar, where Sam and Ruby stood.

“Hey Sam! So, is this your date?” Jo smiled warmly.

Sam looked to Ruby, excited for the two women to meet.

“Yes I am,” she chuckled, extending her hand to shake Jo’s. “I’m Ruby.”

“Jo Harvelle, bartender and assistant manager. My mom owns the place.” She paused, realizing that Sam and Ruby didn’t come here to listen to her biography. “Well, I'll take you to your table.”

She briefly left a waiter in charge of her post at the bar, and motioned for the couple to follow her. Ruby expected her to take them to one of the regular two place round tables, but Jo led them into a room Ruby suspected wasn’t for dining at all. It looked more like a private dining room, she assumed part of the Harvelles’ home.

On the small square table lay a white tablecloth, several candles providing romantic lighting, and a vase with several roses. Fine china plates and silverware were placed in front of the chairs, as well as a bottle of very expensive looking wine, and pristine crystal glasses.

“Special request,” Jo explained, looking at Sam. “For a very valued customer.”

She left swiftly, closing the door gently behind her, to leave Sam and Ruby in the privacy of their own 5 star dining experience.

Ruby realized only then that her eyes were tearing up. She hadn’t expected anything like this. Sam planned it all, went to all the trouble to give her a dinner date right out of a romantic comedy. He looked at her like he wished he could do something even more; as if it wasn’t enough to invite her on the sappiest romantic date, take her home and make love to her, when she was going to be the woman roofying him and dragging him into an abandoned warehouse to be tortured. She wasn’t completely sure if she was crying of happiness, or shame.

“Gosh, Sam, this is too much…” she said breathlessly, running her hand through her hair. He raised the pad of his thumb to her cheek and wiped a tear away.

“You deserve nothing less. All I want is to give you the happiest night of your life.”

He already had, and she hadn’t even taken his pants off yet.

Sam held her hand and she gracefully sat at her place, and he followed. His hazel eyes were wide and practically sparkling in the dim candlelight, completely enamored of her.

“I ordered some salad and cheese pizza for us, I mean that’s the fanciest I could really get here, and I didn’t know if you were vegetarian so it seemed safe… but you’re not vegan, are you? Cause if so-”

“Sam!” she interjected, amused by his unnecessarily  nervous rambling. “That sounds delicious. You’ve gone above and beyond on everything.”

Just as she finished speaking, a middle-aged woman with voluminous highlighted hair, wearing a  
leather jacket and jeans approached them.

“Hey, I’m Jo’s mom, Ellen. You must be Ruby!” she patted her on the back, already feeling perfectly comfortable. Any friend of Sam’s was a friend of hers. She noticed the closed bottle of wine on the table and unscrewed it for them, before carefully pouring the deep red liquid into the wine glasses.

“Well, I’ll give you two lovebirds some privacy now. Your salads should be ready soon.” She smiled, in a very similar way to Jo, and made her way back to the restaurant part of the building.

Ruby took a sip. The taste was very strong, bitter at first, but left a sweet afterthought in her mouth that reminded her of cherries. It was wonderful.

“Hey… Ruby?” Sam began. She put down her glass to move her attention to him.

“I just realized… I don’t know your last name.”

Oops. Ruby hadn’t even thought that far.

“Uh- Masters. Ruby Masters. I feel so dumb for forgetting to mention, all this time!” she played off her lie with a chuckle.

“Don’t worry about it!” Sam assured her, just as Ellen delivered their salads.

When she left, and they began to eat, he began again, in a lower, more solemn voice.

“Look, there’s something I want you to know about me, and I know it’s a lot to tell you at once-”

Ruby dropped her fork loudly on her salad plate, interrupting him again.

“Are you a virgin?” she whispered, clearly shocked and almost disgusted.

“No! No way, nothing like that,” he laughed. “Calm down!”

Ruby shook her head, giggling to herself at her own overreaction. Honestly, with her worst fear out of the way, the only thing that could really freak her out was if he admitted to being a brony.

Sam took a deep breath, taking a moment to gather himself.

“I… haven’t been on a real date in a long time. I’ve like, hooked up, but it was never romantic.”

“How long?” she wondered out loud.

“Four years.” He paused and watched Ruby let that sink in; she didn’t really seem that weirded out, and that made him feel better. He saw that as an invitation to explain.

“When I started college I went to Stanford, and for three years I had a girlfriend, Jess, and when we were 22 she died when our dorm burned down. After that, I couldn’t stand being there, or even studying English. I wanted to be an author, but writing reminded me too much of Jess. So my dad sort of decided my life for me from then on out. I switched my major, I moved to New York, I started over.”

“I’m… so sorry Sam,” Ruby tried to say understandingly, but she knew she could hardly reach him, seeing the pain in his eyes as he had to recount the darkest moments of his life. She tried desperately to hide her desire to just die, then and there, swallowed more and more by the gravity of what she had signed up to do. It was more than a political strategy, and she wished she could kill Lilith and Lucifer for even daring to hurt this man over a situation he was hardly involved it. It was psychological warfare that could only parallel that of the blood-thirsty characters on Game of Thrones.

Sam opened his mouth again, speaking less to himself and more to her this time.

“I don’t want to scare you, ok, but you are the first woman who I’ve really had feelings for since then.” He took her hand gently, and looked into her deep chocolate eyes with the tenderness of a wounded puppy. “So if this goes anywhere, I need to know that you’re ok with that.”

“Of course I am,” she responded slowly. It was kind of ironic he thought _he_ was the one in this relationship with baggage.  “I know what it feels like to lose someone. I mean everyone does, but… my parents died when I was 10, in a car crash. I was in the backseat, and i was fine, but i watched them die and... it was awful."

For the first time in ages, her story was true. She knew deep down that she wouldn’t have had such a shitty adolescence if they had been there to raise her, instead of cold and borderline abusive foster homes.

“Ruby, I can’t imagine what that must’ve been like,” Sam responded to her loss. “I guess the cherry on top of my sob story is my mom died when I was only 6 months old. But I don’t remember anything. I don’t remember her at all.”

 _Oh gosh,_ Ruby thought to herself. Sam was totally a wounded puppy, trapped inside the body of a tall, masculine guy.

“We're pretty much the poster children of young adult fiction,” she said, jokingly admiring Sam like he was on the cover of a John Green book. He laughed at her comment even through the sorrow that had come over recounting sad memories.

Their dinner was hardly a traditional date. They ate their pizza, drank their wine and poured their hearts out over just about everything. Ruby talked about her younger sister, Anna. They were together for a while in the foster system until Ruby tried to run away from their current guardian when she was 15, but after that they were separated. When Ruby was 17 and a 14 year old Anna tried to reach out to her, she refused, and when Ruby was the one who wanted to reconnect, her sister was 20, in college, with a boyfriend named Gabriel, and wanted nothing to do with the girl who abandoned her. It guilted Ruby every day.

Sam listened intently and was almost alarmed at how deeply his heart swelled for her. He had known Ruby 2 weeks, and it felt like centuries.

They ate a rich chocolate cake, drank a lighter white wine for dessert, and as they got more intoxicated, the conversation moved to lighter subjects.

“You’re so cute when you’re tipsy!” Sam laughed, observing out loud, as if Ruby’s cocky sense of humor was endearing.

“I’m not cute!” Ruby protested. She had always viewed herself as definitely feminine, but in a dark, mysterious sort of way, not the giggly-ditz-at-a-party way.

“Ok then, you’re incredibly sexy,” he corrected.

Ruby put her elbows on the table, losing all semblance of etiquette.

“We should totally do it then watch Game of Thrones,” she suggested. It started as a joke but as the words left her mouth she was dead serious.

“What episode are you on?” she followed up.

“I blew through the end of season 2 and beginning of season 3 this week. The next one to watch is…” he looked to the side, racking his brain. “Episode 9! The Rains of something…”

Ruby interrupted him swiftly, remembering instantly the gruesome events of that installment.

“Maybe not that one… no spoilers, but uh- brace yourself.”

Sam looked mildly scared, but burst into laughter again anyway. He threw his head back like a carefree little kid, amused by even the simplest humor. She, on the other hand, wasn’t feeling so innocent right then.

Ruby hopped out of her chair and approached him, loving the way his face changed from a confused expression to a happy smirk, and how he sighed with his deep, sensual voice as she climbed onto his chair on her knees, straddling him. Sam could hardly control his desire when her pouting lips drew slowly closer to his. What had begun as a old-fashioned, romantic dinner was totally gone. This was the appetizer for what was to come back at his place.

He fiercely closed the gap between them, smashing his lips against hers frantically and weaving his fingers into the hair at the base of her head. She gasped for air but he pulled her back, pressing her body tightly to his. Their kiss was messy, rough, and yet so perfect. Everything felt right, like they were born to make out on a chair in the midst of a classy dinner. That was them, in a nutshell.

She grinded against him and moaned, tracing her hands up and down the fabric of his shirt, grasping at it as if she wanted to rip it off his body. Instead, she fumbled with the buttons of his collar.

“Take me now Sam, right here,” she begged, breathlessly panting with her lips hovering just above his ear. He didn’t stop her even though he knew he’d have to eventually. He wished he could just push her onto the floor and make love like there was no tomorrow. But this was the Harvelles’ kitchen! It was rude enough they were making out and grinding in their fancy clothes, probably on the edge of knocking something over. If Jo walked in she’d start laughing and kick them out; if Ellen caught them- Sam didn’t want to even think about it.

Ruby had managed to unbutton his entire shirt when he pushed her hand away.

“Sammy…” she protested, whining in a voice he had never heard her use.

“Wouldn’t you rather save this for my place? We can’t do it here, Ruby.”

She gave in, seeing that she couldn’t let her drunken sex drive cloud rational judgement.

“I’ll ask Jo to drive us home,” Sam added, lifting her off his lap and straightening out his pants, as she did her dress.

The bartender was reluctant, but eventually agreed. Seeing Sam so happy and eager to take home such a sweet girl made her feel like she was doing a good thing for him. More importantly, they were probably somewhere around the legal blood alcohol level for driving, and she didn’t want a car crash on her hands. The three of them hopped into Sam’s car; Jo rolled her eyes knowingly when the couple tumbled into the backseat together, lips still locked in a passionate kiss. They paused only to fasten their seat belts.

Jo was ultimately ok with chauffeuring Sam and Ruby. It was pretty entertaining watching them attempt to engage in light foreplay when they were constrained by the belts.

Sam’s hand was hiking up Ruby’s dress, grabbing her ass, when their driver pulled over in front of his apartment building.

“We’re here!” Jo announced, intentionally loudly, alerting Sam and Ruby to the fact that they had arrived.

The two of them shuffled out of the car, graciously thanking Jo. Sam grinned at her in a way that definitely let her know how much she had helped, not only by driving them, but by helping him arrange their date in the first place.

"I'll drop the car off in the morning, k?"

"Sounds good," Sam replied. Jo knew this conversation wasn't his priority.

She rolled down the window as they walked hand in hand towards to entrance to the lobby.

"Be safe!" she shouted, somewhat seriously but mostly just to embarrass them. Sam was a responsible guy, and truth be told, she was happy he was finally putting himself out there again.

She had never seen two people so in tune. Ruby was so different from Sam; harsher, a bit more reserved, and she didn't seem so warm when you first met her. But they shared a fundamental sort of yearning Jo couldn't quite put her finger on. Whenever she had come to check up on them, they were in the midst of a conversation about something really emotionally heavy, like the death of family members. It was a little weird, but sweet. She'd never had a first date like that.

 _They're sure in for a fun night,_ she thought to herself, and she watched them through the glass; Sam threw Ruby into his arms as they entered the elevator inside the building, both of them laughing all the while.

 

 


	4. Shattered Glass

**Notes for the Chapter:**

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> Hope you guys enjoy this chapter! It's 90% smut so if you're not into that just skip to the last several paragraphs.  
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Everything was a lustful blur until Sam had Ruby pinned against the wall, lips locked, hands grabbing and squeezing, out-of-breath moans escaping both of them. And yet, he wanted to be closer, feel her warmth pressed even harder against him. He grabbed her thighs and hooked them around his waist as his hands traveled under her dress.

Ruby’s responses were even hotter than he could’ve dreamed. She sighed and panted his name when he began to unzip her dress, all the while sucking on the soft skin of her neck just below her jaw. He let go of her briefly so she could slide the rest of it down her body, and she did so hastily, with absolutely no concern for the condition of her expensive clothing. The garment fell easily from her hands onto the carpet beside them as Sam took her in; she wore nothing but a lacy black thong, not even a bra. Her breasts were pert and perfectly rounded, begging to be caressed.

Feeling overdressed, he removed his tie, his suit, his dress shirt already completely unbuttoned thanks to her, until nothing covered his upper body. Within a second of seeing his contoured muscles, shining with sweat, Ruby couldn't hold back from jumping him again, capturing his lips once more in an impassioned kiss. She pulled him close with her arms wrapped tightly around his neck, freeing his to fondle her, and gently roll his thumbs around her nipples.

Ruby could easily feel his throbbing cock against her, even through his pants.

"Don't be shy Sammy," she cooed as she ran her index finger from his belly button to his fly; she loved treasure trails on guys, especially ones as buff as Sam. His head fell back and he let out a heavy exhalation when her finger found his tip.

Ruby couldn't coordinate unzipping his pants while she was still straddling him against the wall. She gently lowered herself, one arm still wrapped around his neck for leverage, and forcefully flipped him around, so his back was against the wall.

She reached up and kissed him; it was soft but drawn out, her lips gently sucking his lower one, her tongue running along it. Meanwhile, she pulled his zipper down, slowly, as to tease him. All he wanted was to feel her grasp his girth and pump him in and out of her hand. He quickly shed his pants and his boxers so she could see it in its entirety. Moment of truth.

She gasped and her face turned to an even deeper expression of lust. His cock was perfection; seven or eight inches, standing up, rock hard, in anticipation for her. Ruby considered sucking him off but she had to have him inside her, and now.

Her eyes were drawn to an attractive couch only several feet away. Nothing got a dick deeper inside than fucking sitting up, straddling him, being able to hold on to the top of the couch to help her hips move.

"Let's take it to the couch," she whispered.

"That's quality leather!” Sam protested, half humorously.

It didn’t matter to Ruby. She strutted towards the couch, hips swivelling sensually, knowing Sam loved seeing her perky ass in the lacy lingerie.

“Guess I’ll just satisfy myself then,” she sighed, playfully disappointed. She knelt right in the the middle of the couch, pressing an arm outstretched straight against the upper cushion so her breasts were in plain sight, as she slipped two fingers beneath the black lace. Ruby closed her eyes and moaned overdramatically, making firm circular motions around her clit, and thinking about all the things she wanted Sam to do to her. It was obviously an attention ploy, considering only girls in pornos made noises that loud rubbing themselves off, but she didn’t really want to stop.

It took a good several minutes to get her way. She eventually opened her eyes and saw Sam slowly pumping his cock in his hand, thoroughly enjoying the sight of her touching herself for him to watch. Eventually he gave in; they'd be careful not to mess up the couch, he'd make sure of it. Ruby was overjoyed to hear the sound of purposeful footsteps in her direction and see Sam, the lust of a jungle cat burning in his eyes, coming to her. She stepped back so he could sit down, but he completely surprised her by grabbing her waist, without warning, and placing her positioned just above his cock. He looked up into Ruby's eyes as she slid her panties down her legs, and smiled. It dissolved quickly.

"Shit," he said suddenly, dashing towards the nightstand where his wallet lay. He fumbled a bit and pulled out a small, square packet.

"Sorry, almost forgot," Sam sighed in relief as he walked back to her, carefully removing the condom from its package. He handed it to her; she grinned she she realized he wanted her to put it on him.

Ruby rolled the clear material down his shaft while he watched, boiling with anticipation. It was a good thing he remembered, because she had been too caught up in the moment to even think about protection.

She kissed his tip gently before she got back on top of him.

"Ready?" he asked.

She moaned in response, "You better fuck me hard Sammy."

With that, she sunk down, exhaling slowly to adjust to his girth completely filling her. It was a stretch, but such a marvelous feeling, any discomfort melted away almost instantly. She extended her arms once more to grasp the upper part of the couch, and he wrapped his hands around her waist.

Sam waited for Ruby’s signal to start moving; given their position, it would be her doing most of the work, but he certainly was going to help out.

With a deep inhalation, she starting thrusting, rising up and down with his cock deep inside. He maintained a firm grip just above her hips. She purred and moaned with increasing volume as her arousal grew, and leaned further forward so he grinded against her aching clit.

Ruby was fucking amazing, but Sam felt like he could never be close enough to her. He changed his position at her waist to curl one arm around her back, one tangled in her silky brown hair, holding on and rocking his hips against hers. There was a certain inexplicable quality of Ruby that drew Sam to her magnetically; some divine combination of her perfume, her smile, her snarky comments, the warmth of her smooth olive skin. He instinctively pulled her mouth to his even while she rode him, and he kissed her with a fervent passion he hadn’t felt in years. She accidentally bit his lip when an electric wave of pleasure radiated through her, but he liked it.

In between their kisses, she moaned a mix of profanity intermingled with Sam’s name, continuously rising in pitch and volume until he almost asked her to be quieter, fearing the neighbors might complain. He sensed Ruby was close to coming, but he definitely was too, and as a policy, he always let the girl come first. Sam gritted his teeth and tried his hardest to keep his cool, but by a certain point Ruby was practically screaming in utter ecstasy and the sheer sound of it sent him over the edge.

As if their bodies were perfectly in sync, she surrendered to the euphoria of orgasm just as he did. Her walls pulsed and he exploded into the condom as they held on to each other tightly, riding the wave together.

After the bliss and fall of climax, they tumbled on to the couch in a sweaty mess. Sam briefly tied up the condom and tossed into a nearby trashcan. Ruby rested her head on his chest, listening intently to his pounding heart, feeling his hand stroking her hair. A tear rolled down her face, and she could hardly tell why.

“Sam…” she whispered, voice breaking a little.

“What? Is something wrong?” He sat up, instantly concerned for her. _Was he not good enough? Did she already regret it? Did she just realize she was a lesbian?_

“Nothing, just… hormones, ya know,” Ruby responded, and he pressed a gentle kiss to her forehead.

“Do you need anything?” he asked softly, running the back of his hand along her cheek. She sighed, closing her eyes, and thinking to herself, This is it. Times up.

“Uh, a glass of water maybe…” she said, rising up on her feet. “Want one?” The words were shaky but she tried her best to hide her nervousness. She was going to put a date rape drug in the water of the man who she just had passionate, blissful sex with.

“Sure,” he responded, clearly not thinking much of it.

Ruby made sure his eyes were closed, and went to fumble through her purse. Her fingers found the secret pocket in the lining of the fabric; in it was a small plastic bag with several little white pills in it. They looked so innocent, pure and small, hiding their awful capabilities from the inexperienced eye.

At his kitchen sink she filled two glasses with water, and placed them before her. Her heart pounded. She didn’t want to do this.  This was the last thing she wanted to do. And yet, she had no choice. Two tablets plopped into the glass on the right, and quickly fizzled out, til the only way she could tell the glasses apart was her memory of which was which. Right is Sam’s, she repeated over and over to herself in her mind.

Ruby collected herself, and holding the two glasses before her, re-entered the room, and placed the non-drugged one on a nearby table. Sam saw her and came, with an outstretched arm, for his drink. She stared up at him with a blank face that was uncharacteristically uneasy.

Truth be told, in those split seconds when his hand reached for the glass, Ruby was drawn to his eyes, as she always was. The sunflowers, so bright and soulful; despite everything this man had been through, he had the wonder of a child.

Her hand went limp, and the glass fell to the floor.

“Woah!” Sam exclaimed, jumping back instinctively so it wouldn’t land on his feet. It didn’t shatter, but naturally the water spilled everywhere.

“Let me clean that,” he offered kindly as his surprise subsided. Ruby’s eyes were still glued to him, and driven by spur of the moment impulse, she threw herself at him once again. Their lips crashed together in a fury of rekindled lust, and she was sure Sam had forgotten about the glass by the time he was kissing her back with equal conviction. Her hands firmly clutched the sides of his head and back of his neck, and she let the thoughts of her assignment dissolve like the pills in the glass of water. They were still there, but- logic was the last thing motivating her. She wanted to be in his embrace once again until the memory of who she really was dissolved too. Ruby wanted to desperately to be the girl Sam thought she was, because maybe then she’d deserve his love.

Sam suddenly broke away and grunted, throwing Ruby into his arms bridal style, and carried her away, presumably to his bedroom.

When she saw the luxurious king bed in the center of Sam’s specious bedroom, she nearly swooned. The outer layer of the sheets was red, elegantly embroidered with gold and white flowers, but not in a way that made it too feminine.

He dropped her lightly onto the surface, looking at her with pure enamoration. Sam wanted nothing more than to make her feel good, to worship her body like it was a sacred treasure.

He slowly climbed towards her, eyes fixated on her soft thighs, and he dove between her legs. With one hand he stroked the soft, tender skin of her inner thigh; with his lips, he made a trail of wet kisses leading up to her core. She sighed and finally let go, resolving that she could forget about everything, just for now; she could easily explain herself to Lilith, and she’d definitely find an opportunity next time she and Sam were together.

Ruby was shaken out of her thoughts when his mouth finally reached the prize. He closed his lips gently around one side of her folds, sucking a little. All he could think was that she was so beautiful, every part of her, and she tasted so good, musky and sweet.

He tried out the whole spelling the alphabet thing on her clit, and she knew, but cliche as it was, it was still incredibly satisfying. A, B, C… and a wave of pleasure radiated through her. She lost track eventually.

She got wetter and wetter when she was close to coming; Sam was making skillful circles with his tongue around all her most sensitive areas, pressed firmly and hitting every spot. Blood was rushing quickly downward, her clit was throbbing, and she couldn’t hold back. Gasping and moaning, she came hard, and she saw him grin with pride as he watched the wild bucking of her hips. Her hands fisted against the thick fabric of the bedspread, her entire body squirming, until eventually she settled down.

“Let’s get in,” Sam suggested, and Ruby obliged. Within a minute or so they were face to face, snuggled under the covers, warm and safe.

“Wanna do it again?” he asked, raising an eyebrow. Sleepy bedtime sex was a treat.

“Of course,” she sighed, and he slowly moved to place himself on top of her.

They made love again, more slowly, delicately, but still driven by the inextinguishable fire of their lust. She would let him take her away all night, love her until they couldn’t help but give in to slumber, and let the night swallow them. They drifted off, Sam curled around Ruby, holding her waist close to him, her hands resting lightly on his. Peaceful, and blissfully unaware of the danger ahead.

...

That was, until her phone rang loudly at 4am.

_Fuck._

Sam was a pretty deep sleeper; the noise only made him stir. Ruby, on the other hand, was instantly woken. She tumbled out of the bed and ran into the adjacent room where her purse was, guided only by the dim moonlight shining through Sam's wide windows.

Of course she knew who it was. At this point, she didn't really care. She was nervous, but she still held the power dynamic over Lilith.

"Ruby.”

“Aw, aren’t you going to remind me your name?” The joke was getting old, but Ruby couldn’t care less if she was being funny or not. Pissing off her boss was the priority. Shoving that stick even further up her ass.

“We missed you. I am a patient woman, but it seems like you’re not making a real effort to be punctual, and I’m having difficulty understanding why such a well-known professional as yourself is failing to kidnap one man.”

“I’m sorry, he caught me putting the pills in. I just said it was medicine for me, and gave him the water without.”

There was no way Lilith was going to buy that.

“You couldn’t use some chloroform once he fell asleep?”

She chuckled nervously.

“He’s still awake, we um- well, what can I say, he can’t keep his hands off me, it’s like he doesn’t even get tired.”

It took some time and a lot of feigned confidence to get Lilith to leave her alone. He was constantly trying to get in her pants, sex with him was boring, she was doing all this to play her role and get him to be more trusting, lie after lie after lie.

“Next time. Then he really won’t see it coming,” she promised, assuring herself she spoke truthfully, but knowing that she would only fall harder from him the more time they spent together. At a certain point she probably wouldn’t even care at all about her million dollar assignment.

She was terrified.

 


	5. Accidental Black Line

_“Next time. Then he really won’t see it coming.”_

It took Lilith several seconds to even process that conversation, considering she couldn’t figure out if this was all some ridiculous joke on Ruby’s part. To think that the country’s most prestigious agent couldn’t even chloroform a guy when he was literally in bed right next to her was laughable.

She exhaled harshly, and pushed a flyaway hair back into place. Lilith had come this far, drove to a warehouse in the middle of nowhere, had her video camera, everything, and that leather-clad bitch had the audacity to stand her up.

She was suddenly aware her breathing had become way too forced. Her therapist advised that she needed to control her stress, for both mental and physical benefit. An important woman such as Lilith could not afford to succumb to people she, at the end of the day, was in charge of. Her eyelids fluttered shut; she practiced her square breaths, calm and calculated, as she pictured the lookout of her summer beach house, convinced herself she felt the soft breeze, smelled the sea- she gave up, still consumed by exasperation. She had no problem using this skill when Dr. Azazel talked her through it!

She needed a distraction, and desperately, before she could drive again. From her Coach purse she pulled a cigarette and a lighter, and leaned the seat back as she let the familiar fumes fill her lungs. Her painted pink lips pursed and blew dramatic grey smoke, enjoying watching it dissolve into the air. Yes, now she could think clearly.

Ruby did deserve the benefit of the doubt. After all, she was something of a legend in the world of privately hired agents. Rumor had it she had shot a Mafia boss right in the heart from the window of another building, and right when he was in the middle of fucking his mistress. The girl was intelligent, she had to give her that. Maybe she had something in store that would even surpass the original assignment; maybe she just got a thrill of playing mind games with guys. Lilith certainly could sympathize.

The bright screen of her phone was shocking at first, but she adjusted. If she had to sleep in her car that night she’d go insane.

“Siri, are there any hotels in the area?”

“The St. Louis Cardinals won the world series in 2011.”

Lilith half groaned, half screamed, chucking the phone into the backseat. “Fucking Siri,” she muttered under her breath.

There was nothing left to do but hit the road, and find whatever was there. Whether sketchy motel or Hilton, Ruby could be damn sure that money was coming out of her paycheck.

…

Sam awoke very slowly, in the way that everyone wishes they could on a lazy Sunday morning. Through the window behind him, a small sliver of sunlight was cast on the wall. Even as he faded from his dreams, most of which were made of nothing but Ruby, his eyes silently admired the stripe.

Everything was sweet and surreal. She lay next to him, so peaceful, lips open just a bit. The sheets covered most of her but Sam’s eyes could follow the curve of her chest even when it submerged. Graceful even in slumber, like Sleeping Beauty, awaiting her true love.

Her eyes fluttered open when she felt him gently kiss her. He pulled away and sat up, gazing at her, tucking loose strands of hair behind her ear.

“Good morning,” she whispered groggily.

“How’d you sleep?” Sam asked in reply.

Ruby rolled onto her side to face him, propped up on her elbow, letting the sheet slide lazily down to reveal her breasts.

“Alright, I guess. You?”

“Good. Probably the best in a while,” he thought out loud, knowing he didn’t really have to explain why. Her lips curled into a knowing smile. She pulled him back down to her and kissed him deeply. Being in bed with him felt so perfect and right, whatever that meant: sleeping, fucking, sappy-sweet cliche love-making. As she ran her fingertips along his muscular back, she felt the crooked lines that stretched down his shoulders, where her nails had dug in as she held him close last night.

His phone buzzed out of nowhere, making an especially annoying sound as it vibrated again the hardwood surface of his bedside table. Neither of them hid their disappointment, but they could certainly resume any time.

“It’s Jo,” Sam told Ruby as he saw the caller ID. “Hey! Are you here with the car?”

He could hear Jo’s chuckle over the phone.

“That depends, am I interrupting anything?”

“No, don’t worry,” he lied politely. “Be down in a sec,”

Jo leaned against the car, wearing her usual outfit of a tank top, leather jacket, and boot cut jeans. Her legs were crossed, hands in her pockets, and she smirked when she saw Sam come down in clearly disheveled clothing.

“Crazy night, huh?” she asked, knowing the answer, just curious to see Sam’s reaction.

“Yeah,” he chuckled, ruffling his hair, looking to the side as he smiled, unable to suppress it.

Jo tossed him his keys and he caught them easily in one hand. He was about to turn around until she spoke again.

“Hey, Sam,” she said, motioning for him to come closer to her. Jo always had that sort of boyish attitude when it came to friendships, all too eager to congratulate him on his sex life. But this was different. She put a hand on his shoulder affectionately.

“I’ve never seen you as happy as you were last night. Ruby’s a good girl, I hope she sticks around.”

“I hope so too,” Sam responded, smiling sweetly when he thought about actually being in a relationship with her. It seemed to be where things were going, for Sam at least. It was too early to say he loved her or anything, but… maybe he did. He could practically hear Dean’s voice in his head telling him what a sap he was. The two of them made a deal when Sam was 17 and his older brother was 21, that if Dean ever got married, he’d give Sam 1 grand. Unfortunately, it didn’t look like that was anywhere near happening.

“Well, see ya round! And if you ever need another special date, the Roadhouse is all yours,” Jo said, interrupting Sam’s thoughts.

“Oh, thanks! Bye!” he called out just as she started driving away. He was lucky to have a friend as cool as Jo.

When he got back upstairs, Ruby was already dressed and applying her make up in the mirror of his bathroom. Sam came up behind her and slid his hands around her waist. He meant it to be sweet but he bumped her elbow a little, and she ended up painting a stripe of eyeliner along her cheek.

He turned bright red as he always did when he messed up. He prayed that she would take it humorously rather than being genuinely pissed.

“Sam!” she whined, playfully slapping him.

“You’ve never looked more beautiful,” he teased, before taking a wet washcloth and fixing the accidental black line. He wiped back and forth several times, before examining his work, and announcing, “All better!”

Ruby sighed, shaking her head at him.

“And they say chivalry is dead,” she chuckled, and found herself compelled to kiss him before she had to go on her way. She slid her hands around the back of his neck and stood up on her tip-toes, capturing his lips with hers moving them together with the electric chemistry they had shared the night before. Ruby knew she couldn’t stay here for so long, but she was so tempted to just rip her clothes off and fuck him again, she could hardly suppress her lady boner. Eventually she had to pull away, but she got to see the eyes she so dearly loved looking into, the sunflowers of green and brown that poured emotion, adoration, everything he felt for her.

“When can we get together again?” he asked softly, as if his heart would break into a million pieces if she didn’t want to.

“Whenever.”

“You can come over anytime this week. We still have to watch Game of Thrones together!”

“Yeah, sure!” she said, feeling a pang of anxiety when she realized she had to drug him then, or she’d lose her chance forever. Lilith would want to kill her. Maybe it wasn’t too late to kidnap Dean instead?

“Tuesday?” Sam suggested, raising an eyebrow.

“Sounds good,” she affirmed, and planted a kiss on his cheek before she left.

…

Dean knew Sam had gone on a date last night with that Ruby chick. He had pretty much given him the cold shoulder since last week when he threw up all over his brother’s car, but Jo told him. Dean had some weird protective feeling over Sam when it came to his dating life, considering this was the first time in years he seemed romantically interested in someone. He’d hook him up with one night stands but it was just a sex thing, Sam didn’t really give it much thought beyond that.

But with this girl, Dean was 110% sure Sam got some last night. It was his brotherly duty to want to hear about it.

Sam took a while to answer but he did eventually. His voice sounded kind of worn down, unexcited.

“What?” he answered, and Dean could tell he expected this call to be something obnoxious.

“Woah Sammy, just wondering how the date went.”

“Oh! It went really well, Jo and Ellen totally went above and beyond-”

Dean interrupted, always there to cut to the chase.

“Sammy. How was _it.”_

Sam chuckled nervously. It was a little weird how Dean seemed to want to know details. Sam suspected he felt like the Yoda to his brother’s Anakin when it came to girls. Maybe he drank through all of Sam’s birthdays and forgot, but Sam was 26!

It dawned on him that Dean’s curiosity probably came from a place of protective brotherly love. He didn’t want him to get hurt. Possibly it was deeper than that; he didn’t want to feel weird asking Sam questions about love so he left it to sex.

“Good, really good. Fuckin amazing man. She even convinced me to do it on the couch.” He laughed, fondly remembering the events of only half a day ago.

"Impressive," Dean noted.

Sam continued. “She’s amazing. It sounds cliche but she’s kind of everything I want, you know? She’s smart, she’s classy, and so gorgeous…” he trailed off a bit. “Do you think… it’s too soon to actually ask her to be in a relationship?”

“You are sure coming to the wrong person with that question,” Dean laughed.

“Come on, you’ve had relationships, whether you like remembering or not. Lisa? Benny?”

Dean sighed.

“I guess just… whatever you say, it doesn’t matter, she’ll know. Am I being too cheesy? Just offer to make love to her in a field of roses or wash her feet or something. Girl stuff.”

“I’ll take note,” Sam responded, somewhat humorously, but it wasn’t really bad advice. Either it would happen or it wouldn't, and  it's not like they could be in this grey area forever.

"Hey man I gotta get to a class. Crowley again," he groaned.

"Have fun," Dean chuckled sarcastically. He was so glad he didn't bother with that college shit. He barely finished high school with a 2.5 gpa.

Sam heard the sound of the call ending. He sort of had the urge to text Ruby but it had only been an hour since they last saw each other. All her wanted was to make smile even when she wasn't with him. Her chocolate eyes had a way of sparkling that— in a super cliche way— reminded him of the goodness in the world that he wanted so badly to believe in. Maybe he could.

...

Ruby found herself, 7 o'clock on a Sunday, where she often shamefully did. 4 shots of tequila in her system, elbows leaning achingly against the sticky wood of the bar table, mindlessly staring at the rack of liquor along the wall.

She wanted Sam. She wanted him in every sense of the word. Ruby had been for 10 years a pessimist undeserving of love, at least in her opinion. Sam was a loving, honest man with eyes as wide and wondrous as a cartoon puppy. More and more she pictured herself just totally abandoning her mission, marching right into Lilith’s office and flipping her off before ripping those million dollars right in half. She could lie to herself a million times but she would lift a hand to Sam Winchester.

Ruby loved him. And holy shit, she was going to start crying, alone at a bar, pitiful and fucked up as a lonely girl can be.

"Hey sweetie," said a husky, unfamiliar voice.

She looked up and saw a guy in a suit that made him look like a Barney Stinson wannabe trying to flirt with her. She scoffed.

"Not interested," Ruby snapped, and threw her purse over her shoulder. She was so fucking done with this guy and he had only uttered two words.

"Hey, relax, just lookin to make friends," he insisted, and maybe if Ruby wasn't so drunk and full of rampant emotion she would've believed him. He wasn't that creepy.

Yet she flashed around and smacked him as hard as her wobbly hand could.

"Friends to go fuck you in your penthouse?!?" she yelled, way louder than necessary.

About 40 pairs of eyes turned to look at her. The room filled with whispers, gasps, a couple cheers, a couple "what the fuck?"s. She instantly regretted it.

The man rubbed his cheek as he backed away from her, speechless, frightened. The bartender approached her, speaking firmly but clearly afraid he would provoke her again.

"Miss, you're gonna have to leave, or someone's gonna press charges."

Ruby felt her chest sink, everything go numb. She ran an anxious hand through her hair, and pulled out her wallet, smacking two twenties on the table and walking away.

She sat on a bench a couple blocks away, cause she didn't want to embarrass herself and have everyone know she didn't even have a ride. Cars whooshed by, colors fuzzy in her blurry vision, tears stinging her eyes and only making it worse. Whether it was from the brisk frozen wind, or the shame, she didn't really care to debate with herself. Eventually she'd have to hail a cab.

Out of nowhere, she felt her purse vibrate in her lap. The brightness of the screen shocked her a bit at first, but she adjusted, and tried to read the text.

 _Hey, how's it going?_   Sam asked in the typical inquisitive white guy fashion.

Should Ruby really tell him? God, he seemed to think she was so classy when they went to dinner last night, all snazzy in her dress and fancy jewelry. She didn't want to burst his bubble. But she really wasn't safe out here, and his apartment was only a mile or so away.

She took a deep breath, filling her lungs with icy air, and called him.

"Ruby," Sam answered quickly. "What's up?"

"Look, I don't want to trouble you, but I need a lift," she began, trying to sound calm. "I'm kinda drunk and kind of stupidly emotional and I just, like, need someone, ok." Her words were slurred and mumbly; she didn't really want to have to be saying them.

"Not a problem," Sam responded.

"I'm so sorry to dump this on you—"

"Whatever you need, Ruby. I'm not one to judge."

"Thanks," she said, sniffling. "I'm outside some sushi restaurant on eighth street... Yoko's."

"Oh, I know that one. Be there in like 15 minutes," he said. "Stay safe."

"Bye," she responded, and hung up.

Sam arrived just in time; Ruby could swear she was minutes from hypothermia.

He came up behind her and tapped her lightly. She looked over her shoulder and saw him, cartoon sunflower puppy eyes and insanely masculine jawline.

"Let's get you home," he said, kissing her forehead affectionately. He could see she was upset, but he wasn't going to push her to tell him about it.

"Can I... stay the night again?" she asked tentatively, fully prepared to apologize for wanting too much from him.

"Of course," he replied, much to Ruby's surprise. "I gotta get going pretty early in the morning but you can stay as long as you want. Just don't steal my tv or anything. Or throw a rager," he said, laughing to himself. Ruby smiled in thanks, already cheered up by his stupid sense of humor.

**Notes for the Chapter:**

> Hope you guys enjoyed the latest installment!
> 
> You know what I'm gonna say xD Please kudos, bookmark, and leave comments! Contact me on tumblr at burningruby.tumblr.com OR adabbon.co.vu, on twitter @Shmeeblez, and email mochafreez@gmail.com.
> 
> If you'd like to take part in editing or proof-reading chapters before they are posted, as usual, message me :)


	6. Fan Mail

With Sam's help, Ruby stumbled her way into his apartment. He guided her onto the couch, the same one they had had sex on last night. Totally different situation now.

"There you go," he said in a calming voice as he lowered her into a comfortable sitting position. He threw a   blanket over her; it was powder blue, with embroidery of little teddy bears, blocks with letters on them, pacifiers.

"Oh my God, do you have a kid?" Ruby asked, honestly not sure.

"No, no," Sam assured her. "This is really embarrassing, but um, it was mine." He sighed deeply, looking at it with a sensitive vulnerability in his eyes. "I don't remember my mom at all, I mean I was six months old when she died, but I have a picture of her, in the hospital right after I was born, where she's got that blanket covering her and she's holding me."

Ruby wanted to say something but she didn't really know what. She definitely didn't judge him, not at all; she understood, probably more than he would've realized.

"At least I remember mine," she began. "Right after the accident, the paramedics and firefighters were trying to comfort me and I was just kinda staring at the wreckage. They thought I had a brain injury or something. So they tried to get me onto a gurney but I was just kicking and screaming, like maybe if I stayed my parents would come back to life. Like somehow by dying they were abandoning their daughters, and they promised they never would."

She paused as she felt the haunting memories trigger tears, real tears, not the weird drunk ones. It felt like a million years ago, and yet, her senses never forgot what they had felt on that frigid September night. Flashing lights, sirens, gaspy breaths as she tried to breathe when the smoky air invaded her lungs, passersby staring in horror at the car as the police tried to push them back.

"Some firefighter handed me a stuffed puppy. I guess that's the procedure with traumatized kids," she sniffled as her eyes really started watering. Sam put an arm on her shoulder; all he wanted to do was pull her in and kiss her until the pain was gone. But how could he, when he was just a walking scrapbook of tragedy?

"For some reason it helped," she said through tears. "I named it Rufus after the firefighter who gave it to me. He stayed with me all through the ride to the hospital, and even sat next to me for a little bit while nurses took my vitals and filled out paperwork and stuff."

She looked at Sam, with little streams of black running down her cheek.

"And- I still have it, right... right next to my... bed..." she couldn't stop it anymore. Ruby fell into Sam's chest and sobbed, not holding back a single tear, sobbing for all those 17 years since the crash that she never cried. He rocked her back and forth, stroking her hair, gently soothing, "Shhh. I'm here. It's okay."

There was no one else in the universe she'd rather have consoling her. His chest was so broad, and warm, and the constant rhythm of his heartbeat called her home, where he was right, she was okay. At least for now.

"You should get some sleep," Sam advised, still speaking in a voice of aching sensitivity. Ruby stupidly reached up and kissed him, needy and unabashed, just needing to feel him in every tangible way. She wrapped herself around him and poured every uncontrollable emotion into their embrace, her hand caressing the back of his head. It seemed Sam had completely forgotten his caretaking role and bought into his own need, pushing with equal force against the soft, swollen lips of the only person in the world who he just knew understood him. As her wet cheek brushed against his, he found himself unsure if kissing her was helping the situation or not.

"Ruby..." he sighed, pulling away gently. Her eyes were wide and sorrowful, full of the pain he had only recognized in himself.

"I'm sorry..." she responded in a cracking voice, shaking her head, and sitting up straight. The blanket slid off her, but her eyes were cast aimlessly downward. In truth, she felt like a user. Anyone who could comfort her through recounting childhood trauma unvisited for years deserved real happiness. Real love. For once in her life, she had to do the right thing.

"Sam," she began, sniffling and trying to blink another round of tears away.

"You don't want me around. I'm a mess, completely unlovable, and you deserve a girl who actually has all her shit together."

Sam shook his head. He took her hand, and clasped it in both of his. They were so large and warm, she could only feel her heart increasingly ache knowing she couldn't keep pretending she could ever really be his.

"No. Ruby, don't ever say that."

She turned to look back up at him, and see his lip quiver a little and his eyes water.

"I care about you. Probably much more than someone should after only a week and a half," he continued, and chuckled to himself. "You don't think I'm damaged goods too? Sometimes I'm not sure if I deserve you. But in 26 years, I've never met anyone who sees me like you do, like I am deserving. So for right now, let's not worry about what we are. I just want to be with you whenever I can, and I hope you feel the same way."

When Sam flashed her the wounded puppy look she was hopeless; so moved she was unable to even form words, she nodded and smiled, letting him grab her cheeks with those big hands and kiss her silly.

The usually fiercely dominant voice inside Ruby, the one that would want to scream when if saw what a lovey-dovey sap she had become, was being smothered with a pillow. She surrendered so completely that any logical thinking was smothered along with it.

"Not the couch," Sam insisted. "Not again."

Ruby laughed and pulled him to the floor. Her needy little hands grabbed the light fabric of his tee shirt and started tugging, eager to pull it off him. She wasn't excited and turned on the way she had been last night, when all she wanted was to have a little fun. 24 hours had passed and now she needed, with a passion she could only describe as completely irrational, to feel him inside her and all around her, and remind herself he was real.

They hardly released their lips as they tore away at clothing. Sam's back was against the carpeted floor, and Ruby lay on top of him, so she had to stop briefly to undo his belt, and remove his jeans. When she did, all that separated their skin was Ruby's lacy undergarments; Sam hooked his fingers around the elastic sides of her panties and smiled as he saw the lustful anticipation in her wide chocolate eyes. They didn't almost forget protection this time, but Sam took care of it much less ceremoniously than he had the first time around. He hastily unrolled the condom onto his throbbing cock with his fist, and pushed deep into her cunt, eliciting a drawn out moan from Ruby. Her hips began to move slowly and she let herself fall back down to face him, to see his flushed face while they shared the pleasure. Strands of her hair fell against his cheek, and she pushed them away so she could keep kissing him.

While she maintained rhythmic thrusts against his hips, he reached around for the clasp of her bra. She'd never met a guy who could actually manage to remove a bra in the single swift motion of movie sex scenes, so she sat up and helped out a little. Sam smirked, like it was an insult to his manly pride, but Ruby made a mental note to later assure him that even she had difficulty taking it off herself. She let the lacy black bra slide down her arm, and tossed it off to the side.

With her hands pressed against his shoulders now, she moaned and grunted, grinding her hips furiously against him. He succumbed to the blissful feeling of wholeness, the immense pleasure of feeling Ruby ride his cock and pin him down. She squealed a little when he reached around and grabbed her perky little ass, helping her thrusting motions and squeezing just because he could, and he loved the look on her face when he did. He tried so hard to get a grip on himself, seeing her eyes flutter every time he hit the right spot against her walls, but a long, low moan triggered his orgasm.

Sam panted hard when he pulsed inside of her. Waves of pleasure he could only describe as euphoria radiated through him, but as he opened his eyes, he saw a disappointed Ruby, hovering above him, looking annoyed.

“How rude,” she sighed, and he suddenly felt guilty because he came first and now she was high and dry. He pulled out and removed the condom before flipping her over and taking a firm nipple into his mouth. She sighed and relaxed once again when she felt his warm, wet mouth against her breast and a finger slip in between her folds, rubbing calculated circles around her clit. Having been close to climax even when he was still inside her, it didn’t take more than a minute to have her coming too.

Ruby screamed and threw her head back, gasping for air. Sam smiled, proud of his work, and laid back on the floor next to her.

“Hope your baby blanket didn’t see that,” she joked, still a little out of breath.

“It should know how babies are made, right?” he responded before really thinking about how that was coming off. She giggled.

He swiftly changed the subject. They were using protection and anyway, he didn’t want to give off the impression he wanted to have a baby, like with her, now. Who knows, if everything worked out maybe… he mentally shut himself up.

“Probably shouldn’t have fucked you,” he admitted. “I mean, you being intoxicated and all. Just promise me you’ll actually remember it tomorrow morning.”

She tapped his nose delicately and smiled.

“How could I forget? Silly Sammy.” He smiled brightly back at her. When Dean called him Sammy after the age of seven he wanted to punch him in the face. When Ruby said it endearingly, he loved it. She continued. “Now let’s get to bed.”

“Woah,” he protested, changing facial expression, but still coming off playful. “No way. You’re on the blow up mattress tonight.”

“Excuse me?”

He held her arm and pulled her so they stood up.

“I already had a drunk throw up all over the backseat of my car. I’m not messing up my bed. You should know by now I take my furniture very seriously,” he said, smirking at a jokingly insulted Ruby.

“And what, you would’ve been fine with me puking in the middle of riding your dick? That'd sure have been sexy.”

Sam rolled his eyes, and picked their scattered clothes off the ground, placing them in a neat pile next to the couch.

“Don’t worry, I’ll be right next to you on the couch, holding a bucket just for you,” he teased condescendingly, smiling and booping her nose, imitating her affectionate gesture.

“Asshole!” she said, pushing his shoulder in jest. Just to annoy her more, he pulled her head forward and gave her a big, wet smooch, effectively ending their playful banter.

“Lemme get you some pajamas,” he said, walking into his room to grab some old sweatpants and a tee shirt, along with the inflatable mattress he kept in the top shelf of his closet. He definitely thought it was cute seeing girls wearing his clothes.

Ruby made her way to the bathroom to clean up a bit and put her underwear back on. Sam was waiting next to the door, holding plaid pajama pants and an old, baggy shirt. She unfolded it and read the words aloud.

“Kansas City Chiefs?” she scoffed. “I forgot they even existed.”

“Well, where are you from anyway?”

“San Francisco. 49s girl through and through,” she grinned proudly. “Didn’t you go to Stanford? You should be more loyal.”

He chuckled, tossing the pants lightly at her face. She flinched as the fabric hit her nose.

“Just put these on.”

Ruby did and laid herself down on the couch. She didn’t feel that intoxicated anymore. Truthfully, she couldn’t really qualify as drunk. 4 shots of tequila? She wasn’t a lightweight.

It wasn’t easy to admit it to herself, but she led a lonely life. And now, just maybe, she had Sam. So after humiliating herself at a bar, she wanted the comfort of knowing at least someone wanted to be with her.

Unfortunately for her, one thing had become abundantly clear. Ruby was at the point of no return. Her purse didn’t even have any of her drugs in it. She would never poison Sam Winchester. When she could get the courage to tell Lilith, or at least escape her wrath, she didn’t know.

...

Mark Lucifer was spending his evening responding to letters his secretaries had given him. The ones they deemed should be responded to by Mr. Lucifer personally.

The most obnoxious one was from a kindergarten classroom in Michigan, his home state. The neat block letters were clearly written by the teacher, but he suspected that the kids had come up with what to say, considering how laughable it was.

_Dear Senator Lucifer,_

_We are Miss Talbot's kindergarten class at Richard Roman elementary school in Detroit, Michigan. Our class is learning about the Presidents and the elections and we wanted to write to you because..._

"Blah blah blah," he said to himself, completely uninterested. He skipped through all of it to read the last line

_We hope you keep making our country a better place every day. Love,_

Every single goddamn kid had signed their name at the bottom in crayon. Kira, Rory, Scott, Arya... some kid named Kurt wrote the wrote in all caps and had the R flipped backwards. It was only a reminder how much he hated children. He reluctantly opened the file he always used to respond to kids, replaced the INSERT SCHOOL HERE with Richard Roman elementary school, and scribbled his name at the bottom.

Just as he finished, he received a call from Lilith. This evening was just one annoyance after another. He hoped she had good news.

"Helloooooo?"

"This is not working out. Little miss leather is getting suspiciously close with Sam."

He moaned, his expectation of good news shattered.

"I'm nauseated."

"One of my spies followed Ruby to a bar tonight. I had him bribe the bartender to stick a tracking device in her phone while the man I hired tried to hit on her to create a distraction. Apparently she smacked him in the face and ran right on over to Sammy's house, and she's still there."

"Jesus fucking Christ," he said, almost at the breaking point of his patience with this little slut.

"Ah, but here's the silver lining. I did a little bit of... investigative work. And guess what? Ruby's nothing but a sad little foster child. She's been a sniper since she was 20, but there's nothing in the social security database on her. I didn't expect to find anything just by searching 'Ruby'. So I used some facial recognition software to narrow it down a bit, and contacted some past clients. I eventually pieced together the sob story of the year."

Lucifer grinned devilishly.

"Go on."

"Lost her parents at 10, fell into a pretty sketchy crowd in her teenage years, and ended up in the company of some San Jose gang members who trained her to seduce and kill their enemies. And boy did I get some dirt on her; Ruby's got a little sister."

He was at first unimpressed with the news of his agent's dishonesty, but they sure had leverage on that little whore now. Still, it didn't help with the plan to get Winchester to drop out of the primaries.

"Believe me, I'm overjoyed Lilith, but how does this help us kidnap sensitive little Sammy?"

His campaign manager chuckled.

"I know the perfect woman for the job. She'll have Sam in that warehouse in no time, and I'll make sure she gets rid of Ruby while she's at it."

"And who might that be?" Lucifer responded inquisitively.

"Abaddon," Lilith said, smiling. "Abaddon Sands."

...

Ruby's head was killing her when she woke up. She wanted to go get some Aspirin but the inertia of the soft mattress was too strong to fight. Damn that stupid baby blanket for being so comfortable.

"Sam?" she called out groggily, with all the volume she could muster.

She saw him peek his head out of the doorway to the kitchen, smiling when he saw her propped up on her elbow.

"Good morning. You want some coffee?"

"Sure,"  she grumbled, stumbling off the mattress and unsteadily onto her feet. He came and handed her a mug full of piping hot liquid. Her head pounded but she knew Sam would have to leave soon, so she’d fight it just to start her morning on the right side of the bed. He was somehow so cheerful, eating a banana and some cereal in his loose pajamas, flipping through his phone.

“How’d you sleep?” he asked, taking a sip from his dark blue NYU mug.

She shrugged her shoulders.

“You were sleep talking last night,” he chuckled. “You sounded, like… terrified. Just saying Lilith a million times. Is that someone you know or something?”

“Um… old friend. We had a falling out a while back," she lied, quickly dismissing the question. Sam nodded as he understood, and took the last bite of his fruit. He stood up and walked back into the kitchen, opening the fridge door wide open for Ruby to see.

"What do you want? All I've got it is a couple more bananas, some Cheerios and whole wheat bread if you want toast," he announced, bending and sticking his whole head in the fridge. "You know what, I'll give you some money if you wanna go to the IHOP a couple blocks away," he chuckled, but she knew he really was offering.

"Thanks but I'm ok with toast... Ya know, easier on the stomach," Ruby said, declining his offer. Maybe another time they could go there together, get some stupid chocolate pancakes, put whipped cream on each other's noses, all the cutesy stuff she hated seeing other couples do. Yet she was kind of itching to be that cliche annoying couple with Sam.

When she went off on a thought tangent like that, she eventually remembered the reality of her situation, and it was like getting hit in the face with a brick. She had no idea what to tell Lilith.

Sam dropped two thin slices of bread into the toaster, and pushed down the lever.  Ruby noticed a little bit of scruff she hadn't last night. Her heart sped up; somehow, even after a late night and early start in the morning, he had never looked sexier.

"I should go take a shower," Sam said, approaching the table and leaning down to eye contact with Ruby. "Sleep, abuse my DVR, I really don't mind."

"Excuse me," Ruby protested coyly. "We should go take a shower."

Sam rolled his eyes and chuckled. He knew he should take it as a compliment that Ruby was all over him, but he did have a class to be at... oh well.

"Okaaaay," he gave in. "Just a quick shower. You- get your toast first!" He pointed to the simple toaster in the corner of his marble kitchen counter, two crisp slices sticking out of its slots.

Ruby smiled as she watched him turn around and walk hastily to his bedroom, beginning to pull his shirt from his toned upper body. A glimpse of his back had Ruby rushing to butter her toast; she could finish it later, once he was gone.

Sam was startled to see her open the textured glass door of the shower, completely naked, absolutely glowing. She was pleased to see its spaciousness, and the fancy removable shower head, which was mounted at its spot high up as Sam ran his hands through his hair, washing out the bubbles of shampoo. His whole body was an intricately carved waterfall in a mountain of smooth, untouched rock. A work of nature too perfect to touch. But that sure wouldn't stop her.

Ruby reached to the rack behind Sam and pulled out a large bottle of body wash, squirting a generous amount into her hands, looking up at him, grinning mischievously. Washing him was a poorly hidden excuse to get her hands on every perfectly crafted part of his body, but Sam wasn't going to protest.

Soap-covered hands found his pecs first. Ruby made circular motions around each of his two broad muscles, washing bubbles form, and rivulets make their way down his body. Next, she lathered his arms, making a point of visibly admiring them as she did. When she moved back to his chest, specifically the lower half of it, she dragged her hands down his abs, her nails grazing lightly against the skin. She found herself on her knees, facing his cock, which was already stiffening.

"I've never seen someone so excited about getting washed," she giggled, and looking up at him, saw him blush a little, and chuckle. A piece of him was still reminding him not to be late to class, but—then Ruby dove right in, putting all of his head in her warm, wet mouth, and he sighed, closed his eyes, completely forgot his train of thought.

Sucking gently, she moaned and ran her tongue all around his tip, eliciting a surprising grunt from Sam. Encouraged, she went ahead and took more in.

Ruby sucking him off felt beyond amazing, but seeing her on her knees, water cascading down her breasts, was half the pleasure. The best part for him was how focused she looked, closing her eyes, enjoying the taste and feel of his sensitive skin. Ruby was not a half-assed lover, that had been made abundantly clear.

More and more blood rushed downward, his heart sped up to the speed of a galloping racehorse, and Ruby sensed it. For the grand finale, she braced herself, and took him just about as deep as she could, bobbing up and down as a little bit of spit trickled from her mouth. A guttural moaning noise pushed Sam way over to edge, and Ruby felt his release, swallowing it happily. A little bit fell down her chin; she wiped it off, licking her fingers like she'd just had a satisfying meal.

"Jesus... fucking Christ, Ruby..." he panted, watching her rise up off her knees, smiling when she saw how much he'd enjoyed the blow job.

Now it was his turn, and he wasn't going to waste any time either.

With his long, lean arm, he removed the shower head, and took her in. She gasped a little when she saw the look of insatiable lust in his eyes. The cartoon puppy was nowhere to be found.

Sam grabbed her by the waist, looking her up and down the way she had before; Ruby had always sensed he had a dominant, possessive side under all that boyish innocence. His eyes told her what she wanted to hear him whisper in her ear— _you're my little fuck toy and I'm going to make you feel so good._

He held the shower head just above her chest. His hands fidgeted with the nozzle, twisting it until he found only the most intense massage setting.

"Fuck," she muttered under her breath, caught in her own fantasies when he lowered her onto the tiled floor of the shower. It wasn't very comfortable, but so sexy she couldn't care less. When she felt him climbing above her, she squealed in anticipation for the feeling of water splashing hard on her sensitive folds, her clit, really wherever. She could come from Sam's facial expressions alone.

Ruby sprawled on the floor below him, he hooked an arm around her thigh, gently pulling her closer to him so as not to actually hurt her. With the perfect angle to access everything in between her legs.

The first pounding sensation of the water hit her out of nowhere, and she moaned as she adjusted to the waves of pleasure rolling through her. She arched her back instinctively, but also knowing Sam would love seeing her chest rise and fall so dramatically, breasts in the air. He slowly, frustratingly, moved the shower head closer and closer to its target zone. Water pounded harder and harder, especially against her clit. He started using his fingers a bit to only add to her enjoyment, at first just to spread her folds and let the water hit the sensitive parts inside, but when his thumb grazed her clit and she let out a moan verging on a scream, he knew he better continue.

His thumb was so strong and firm against her, and in combination with the massaging water, fiercely pounding against every tingling nerve between her legs, Ruby was hopeless. Her hips bucked wildly, thrusting her upper body into the air even more, screaming and panting Sam's name. As she settled down, he twisted the top of the shower head to put it on a lighter setting, and turned it off.

She sat up, hair plastered to her cheeks, looking exhausted, but completely spent. Sam had already stood up, and was reaching to grab a towel from the rack directly outside the glass door. Squatting down again, he smiled and ruffled Ruby's hair, making her giggle, sad crinkle her nose in the adorable way he loved.

They dried each other off once they got out, kissing when Sam used his towel to wrap it around her, and pull her close so their bodies were pressed together. It was sweet and simple.

At least he'd make it to _half_ his class.

When they were all dressed, Sam looking spiffy in his white shirt with faint blue stripes, Ruby knew he had to get going.

"I'll be back at noon, but I hope you don't mind getting home on your own. My dad's coming over and.. things haven't really been great between us lately, so..."

"Sam!" she interjected. "I'll probably be heading soon anyway, I feel much better, and I don't want you worried I'll ransack your apartment or something."

"Well, if my apartment has to be ransacked by someone, I hope it's you," he smiled, kissing her cheek. "Still on for tomorrow afternoon, right?"

"Of course."

He left swiftly, and she sighed. Ruby wanted nothing more than to collapse on his soft, warm bed, to rest her head on pillows that smelled so much like Sam Winchester, and drift off with him.

 

 

 

**Notes for the Chapter:**

> I hope you enjoyed this latest installment! (It's my favorite chapter so far... they just keep getting better and better!)  
> Comment and let me know what you thought! Especially f you have an predictions, so I can kick back and cackle evilly as I read them.


	7. Something Like That

“Eve, my nails aren’t going to paint themselves!”

The exasperated voice of her aunt rang through the marble halls of the Knight mansion. Eve sometimes wondered if that woman was capable of any tone of voice besides that demanding, and still distinctively feminine, command. Reluctant, but knowing she didn’t have much of a choice, she pulled her long dark hair into a bun and grabbed the black Prada bag full of at least 100 nail polishes, yanking it from the top shelf of her aunt’s closet.

Abaddon sat, legs crossed, perfect posture, perched in a Victorian chair in one of their house’s many living rooms. Always a bit nervous around her aunt, Eve stood in the doorway silently, holding the bag in front of her chest, praying Abaddon would notice her before she looked foolish.

“Did my brother never teach you it’s rude to hover in doorways?” she asked, putting her magazine down and raising her eyebrows.

“Um… sorry, Abby,” Eve said, forcing an apologetic smile and making her way to the edge of the chair in which Abaddon sat. She zipped open the bag and let her aunt get a good look at her color options.

“Dark red, sweetie. Always dark red,” she smiled condescendingly.

So why does she have so many colors? Eve thought to herself.

“You should know me by now!” Abaddon added, chuckling, but it wasn't meant to be endearing.

Truth be told, Eve didn’t actually know her that well. Not because she had no opportunities to; Abaddon and Henry were always at dinner parties. It was just that she didn’t particularly want to spend time with her. Eve knew perfectly well that Abaddon and Cain, her father, had hated each other since childhood. The friendship between their families was nothing more than a facade.

And yet her father dumped her at his dreaded sister’s house just so he could take his ditzy new girlfriend to the Bahamas!

One by one, Eve painted the glossy polish onto Abaddon’s toes. The smell was awful of course, but she always thought it looked kinda cool, how the brush clearly made stripes at first, but slowly the liquid unified into a smooth, even surface.

Some classical music played out of nowhere and Eve realized it was her aunt's phone. She stopped, timidly looking up as Abaddon picked up the device and examined its screen for the caller ID. When she read it, she seemed, for the first time in her life, intimidated.

"Excuse me for a second," she said to her niece, curling her bright red lips into a smile, revealing her flawlessly whitened teeth.

Abaddon needed to go where no one could hear her. She never knew what Lilith would have to say, but it was never just a quick hello. Her cousin had been extraordinarily busy lately with the campaign and spoke of nothing but it. It wasn't Lilith that scared her though. She was calling from her secret number, which meant something concerning.

"Hey, Lily, how are you?" Abaddon began, physically adopting a confidently joyful facial expression.

"I need a favor."

"Mmm, and what might that be?" she sighed, as if inviting Lilith to blackmail her into one of her illegal political games, and closed the door to her room behind her.

"Robbery? Kidnapping? Extra-hard spanking?"

Abaddon caught her reflection in her mirror, specifically a smudge of striking red lipstick extending below her lower lip. She puckered and wiped it away while she waited for Lilith to speak again.

"Mark and I have been working on something... and it hasn't gone according to plan. We hired the girl who was supposedly the absolute best in the country, and all she had to do was seduce a prep boy and take him to a warehouse where we'd take care of the rest. Then she had the stupidity to go fall in love with him, and well, long story short, we need to get rid of her, and loverboy, we have other big plans for."

Abaddon laughed coldly, the kind of mocking chuckle that made her grin with her mouth open.

"You know that's not what I do. Bye Lily," she asserted, about to hang up, until Lilith interjected.

"I thought you might be hesitant. Let me sweeten the deal. How does a million dollars sound?"

Abaddon sighed, considering. With her fingers extended, she examined her wedding ring, and its magnificent diamond, 1.5 carats, glistening even in the indoor lighting. Nothing boasted her wealth more that the gem upon her ring finger; she was the last person on earth who needed that much money, but she couldn't suppress the thirst for more that always lived inside her.

"I'm listening."

...

"A picnic? Really?" Ruby laughed as she saw Sam folding a dorky checkered blanket and sticking it into a woven wooden basket. He had answered his door with all the supplies in hand, grinning, wearing a plaid shirt that totally clashed with the checkered pattern, but was hot nonetheless.

"Why not? The weather's not bad, and I made some killer sandwiches," he replied, and opened one side to show a sub wrapped in clear plastic. Ruby had to admit, it did look tasty.

She was a little apprehensive about going out in the open with Sam now. A part of her wanted to be relieved that she was technically off the hook from Lilith, but it really was too good to be true. Only an hour ago, her boss had called and informed her that the plan wasn't in fact going through, that opinion polls were rising by themselves due to a new ad campaign and a kidnapping was determined to be too risky. Ruby couldn't have imagined hearing those words in her wildest dreams; she wanted to stay with Sam, more than anything in the world, and she couldn't lie to herself anymore.

"Alright," she said, smirking and grabbing her purse off the floor. Sam offered his hand to her, and she gave him hers.

They settled on a little park a mile or so away. Most of it was a playground, but beside it lay a patch of lush green grass, protected by the shade of a wide-trunked oak. Sam unfolded the blanket in front of them and plopped himself onto it.

“Turkey or ham?” he asked, pulling each of the sandwiches out of the basket to offer to Ruby.

She sat down closely beside him, and grabbed the turkey, answering his question wordlessly. He smiled at her as she took a bite and chewed it slowly, waiting for her response to his creation. Quickly her facial expression turned to amazement when she tasted the harmonious combination of the meat with Swiss cheese and a mysterious sauce.

"Wow," she commented, food still in her mouth. "You weren't lying!"

Sam chuckled and blushed a little.

"You've got a little sauce on your..." he began, pausing to bring his thumb to Ruby's chin and wipe the dribbling condiment from her chin.

"So, there was something you wanted to ask me?" Ruby changed the subject, remembering their phone conversation they'd had last night arranging this date. She knew Sam well enough by now to realize he took initiative in planning their outings; he was a traditional dater.

"Oh, right!" He adjusted himself so he was down on one knee, and paused, looking into her eyes soulfully as he waited for her to react.

"Will you, Ruby Masters," Sam began slowly, making his words sweet and melodic as if reciting a love poem. Ruby looked like she wasn't sure what to make of this.

"...loan me season 3 of Game of Thrones on DVD?"

She pushed his shoulders down playfully, scoffing at his humor, causing him to fall back onto the blanket. In response, he grabbed her arm and pulled her with him, both of them laughing at their own childishness.

"You weren't fooling me," Ruby insisted teasingly.

"I don't know, you looked pretty freaked out for a second," Sam responded coyly, shrugging his shoulders.

Ruby found herself once again fascinated by the range of demeanors Sam Winchester was capable of, and how she couldn't decide which she liked most. She had seen him so sensitive, looking like a wounded puppy, and yet he was a vicious animal in bed. His playful side was so charming and endearing, and for some reason she couldn't figure out, a complete turn on.

She pushed her body to roll on top of him, and began gently kissing him, one hand holding the side of his face. His lips tenderly closed around her lower one as he felt her sigh, warm breath against his cheek. Knowing they couldn't let it continue, considering the nearby playground where some eight year olds were having a birthday party, Ruby kissed his nose and slid back down beside him.

Sam felt a surge of affection that wasn't unfamiliar, but grew stronger each time he was with Ruby, this incredible girl, unlike anyone he'd met in his life. He couldn't deny seeing a bit of himself in her; that smile that for so long hid the pain of childhood tragedies, tumultuous teenage years and admittedly lonely adulthood. Behind her chocolate eyes lay a world of mystery he only wanted to dive deeper into. How he was supposed to, Sam had no idea. Instead, he did the most impulsive thing he had done in ages.

"Do you want to, um... make it official?"

Ruby was caught off guard a bit. She wanted nothing more than to spend time with him, maybe forever, but for some reason the prospect of a real relationship was frightening.

"Like... for me to be your girlfriend?" she clarified, masking the panic surging through her, and the conflicting joy.

"Yeah, something like that," he replied, smiling boyishly as his cheeks turned slightly pink.

Ruby looked over his head for a split second, and her heart stopped dead. The moment froze as it did when she noticed something wasn't sitting well with her.

Leaning against a tree was a sharply dressed woman with flaming red hair falling over her shoulders, designer sunglasses hiding her eyes. It wasn't like she hadn't noticed the woman before that moment, but Ruby had become incredibly perceptive through all the years of mastering her profession. That ginger hadn't turned a page in all her time reclining there, and even more suspiciously, Ruby could make out a tiny bug in her ear, which she was clearly attempting to hide with an elaborate hairdo. She had Lilith written all over her.

"Uh- I want to, I just need to think about it..." she began, trying to change the subject so she could think clearly about what to do next.

Sam looked a little disappointed, but he definitely tried to suppress it, not wanting to push Ruby to anything.

"Yeah, of course, I get it, I just really like spending time with you and I-"

"We should go back, I don't feel well," Ruby interrupted, completely lying, but desperate to get out of there. Sam's face turned quickly to concern. He sat up and put a hand on her shoulder.

She felt bad that she had to ruin the date he had clearly put a lot of effort into, but this was for his safety- for both of theirs. As she rose up, she tried to seem a little wobbly so he would buy it. Sam turned away from her only to rewrap the sandwiches and fold the blanket.

"Are you gonna be ok in the car?" he asked, worried more about her than the state of his car. For some reason, he'd much rather Ruby throw up in his car than his brother, because she would probably be responsible enough to clean it up.

"Yeah, just pull over if I need it."

The moment they got back to Sam's apartment, she dashed into his bathroom, shutting the door behind her. Maybe it was overkill to fake illness this much, but she couldn't let Sam have any reason to leave the house without her.

She grabbed a cup off the counter, scooping up toilet water and pouring it back in as she coughed harshly, flushing every so often. Sam knocked on the door, naturally very worried for her, but in between feigned coughs, she told him she was an absolute mess and she could handle it.

He wanted to help her through it, but if she wanted to be alone, he respected that. She deserved some space from him anyway, considering she wasn't as eager to make their relationship official as he was. Maybe that was just who she was, maybe she had had a bad break up recently or something. He cringed when he heard her vomit again, picturing her looking so distraught, wanting to hold her hair back and comfort her....

Suddenly Sam's thoughts were spiraling.

The clues were everywhere.

She was throwing up, she was hesitant to become his girlfriend, she hadn't told him much about her recent past—Ruby was pregnant. And it wasn't his. The timeline just didn't match up.

Sam sighed, waves of shock washing over him, and he sank down into the couch. He had no idea what to do. He didn't want to straight up confront her but—oh God, he couldn't bear listening to her suffer like that.

He knocked on the door, trying not to be too forceful.

"Ruby, I just want to make sure you're ok."

Ruby resolved that he wouldn't be leaving the house anytime soon considering how worried he seemed to be. She placed the cup back on the counter and let him enter the bathroom.

Sam sunk down to his knees and embraced her, trying to be delicate, but wanting so badly to let her know she had his unconditional support. He released and saw her eyes were watering a little, and she was kind of pale.

"I have to ask—are you pregnant?"

Ruby definitely didn't see that coming. She realized then that it kind of made sense he would jump to that.

"No, Sam, we started banging two weeks ago," she assured him, trying to get him to stop jumping to conclusions like that. "Did you sleep through seventh grade sex ed?"

His gaze fell to the floor, and he bit his lip a little, as if he wanted to say something, but couldn't phrase it. Ruby felt awful; he probably thought she was tearing up because she was, in fact, pregnant. In reality, she found herself almost wishing she were, for nothing but the heartfelt sympathy he gave her.

"I... I know it wouldn't be mine. And I don't know if I can raise a baby, but I wouldn't just abandon you because of that. If you want to get an abortion, I'll be there too."

He spoke to her like he feared she'd leave him; and Sam did. He felt stupid for assuming she even wanted something long term, yet he couldn't picture himself with anyone else, waking up in the morning next to anything but deep chocolate eyes, smooth olive skin, and dry sarcastic humor.

"I got my period yesterday, I promise, I'm not pregnant," she said, and expected his facial expression turn to relief, but he still looked into her eyes like he would give her the world in an instant.

"Sorry for freaking out," Sam apologized, seeming a little ashamed for it.

"No, it's ok, I would too," she assured him, taking his large hand and in hers, rubbing the skin affectionately, tracing his veins. "You'd make a great dad someday."

He instinctively embraced her again, burying her face in his broad, warm chest. She didn't seem to be nauseous anymore. Whatever was bugging her stomach must've gotten out of her system; he certainly hoped it wasn't his sandwiches. After a minute or two, he felt the vibration of her mumbling something against him, and loosened his embrace so he could actually understand her.

"I'd... love to be your girlfriend."

The words slipped from her easily, causing her to finally feel a sense of release. With her confirmation, she threw caution to the wind in every way, and she made her decision, once and for all. Lilith could offer her anything and it wouldn't make a difference. She knew that she was being selfish, dragging Sam into what she suspected was a new and improved plot that targeted both of them in some way. A glimmer of hope still let her believe that she could just leave everything behind, all the spying and kidnapping and smuggling and every sort of crime, and just be the girl in Sam's arms for the rest of her life.

"I love you," she whispered, not caring if he heard.

After a pause, and a kiss pressed against her hair, he whispered, "I love you too."

Ruby was Sam's, and no one else's.

**Notes for the Chapter:**

> Hope you enjoyed this installment!
> 
> Next chapter's gonna be HELLA INTENSE I'll be putting trigger warnings at the beginning of it :) but I think you'll all love it!


	8. Flying Robots that Kill People

**Summary for the Chapter:**

> the chapter title will make sense later, i promise. i just wanted to be silly xD

It had been 5 days since the whole pregnancy scare thing- Sam was still kind of apologetic, but Ruby told him firmly he really didn't have to get worked up about it. After all, she now knew that he loved her and as much to her surprise as his own, Sam knew that Ruby loved him.

Considering her arrangement with Lilith was out the window, and Sam was her only ally, Ruby decided there was no going back. Even if she had never truly been vulnerable with a guy before, or even knew what all that entailed, she figured she could start by showing him her place. She had to begin somewhere and sharing her sanctuary with him, her one true place of solace felt right.

The moment he saw the apartment building he was impressed.

"Wow... Who even lives here?" he wondered out loud as his head tilted up, eyes following the tall building, its pristine glass windows reflecting the sunlight like a mirror.

Ruby chuckled.

"Some 15-year-old named Krissy Chambers. At least, when she's not in Hollywood filming her show on Disney Channel."

Sam responded with an amazed facial expression, amused his girlfriend lived near a B-list celebrity.

"Don't be impressed, the show is terrible," she told him, reaching for his hand as she changed the subject enthusiastically. "Now, let me show you around!"

They strolled through the lobby, swinging their hands, which began as a silly gesture of affection,  but they both secretly liked telling the world they were together. Even Ruby, who for the first time realized that maybe, just maybe, this was her first step into a normal life. At least once she figured out what her dreaded ex-boss was up to, and took care of it.

In her peripheral vision, she saw the back of a head, cascading red hair, belonging to a woman sitting in an armchair.

When Sam and Ruby entered the spacious glass elevator, which matched well with the exterior of the apartments, she pressed the button for the 12th floor.

"Guess that gives us lots of time," he said raising his eyebrows and smiling, as his hands slipped around her waist. She wrapped hers around his neck, and leaned against the wall.

"Seriously Sam? This is completely see-through all the way around." she said gesturing with her eyes and being overly dramatic on purpose.

He kissed her anyway, and she hardly resisted. The thought of getting noticed turned her on a little, especially when his hand migrated to her butt, and she pulled it away teasingly.

"Patience, Sammy," she said coyly, winking, before joining their lips once more.

The elevator dinged cheerfully when they reached Ruby’s floor. Sam playfully chased her down the hallway until Ruby came to a stop in front of her door.

She chanced a quick glance behind her as she swung open the door. She looked down and was greeted by a dead, mutilated bird.

"Jesus fucking Christ," she moaned, rubbing her temples and tossing her purse on the ground. Meg sat happily in front of her welcome present, waiting for thanks from Ruby. Sam just laughed hysterically at her exasperation.

"Ok this is why I'm a dog person!"

She slapped him on his upper arm.

"Just for saying that, you're taking care of it!"

“No way! It’s your cat! What are you even supposed to do with a dead bird anyway?” Sam scoffed, motioning to the carpet where the animal lay. Ruby was already making her way to the fridge, pulling out a beer.

“Why don’t you call 911 so they can do some little birdy CPR on it?” She smiled sarcastically, and waited a second before speaking again, enjoying watching Sam being annoyed rather than dealing with it herself. “Put it in a newspaper bag or something and throw it out,” she sighed.

Sam rolled his eyes but did as she told him. He quickly picked up the bird with an old plastic bag and threw it in the bin without even a flinch, handling the situation much more maturely than she expected. He made his way to the bathroom and Ruby heard him running the tap for a minute or so, thoroughly cleaning his hands of whatever mutant diseases the bird might’ve had. Meanwhile, she plopped down on her recliner in the next room, popped the cap open and took a long swig. The chilled, bubbling drink had her instantly relaxing.

Sam returned shortly, and Ruby pretended not to noticed. He placed his hands at the top of the chair and swooped around so he could see her, grinning now that the pesky bird problem was out of the way, and he could _intimately_ get to know her place.

“So,” he began. “Where’s the bedroom?”

“Anywhere you want it to be,” she replied with a flirtatious wink.

“Seriously though.”

Ruby smiled and took his hand, leading him past the kitchen, the spacious bathroom, a dark room with a bunch of black cabinets and safes he wasn’t sure what the purpose of was, to a bedroom laid out similarly to his, but radically different in interior design. Hers was incredibly well lit, her bed had a soft silvery veil surrounding it, blowing gently in the breeze of the open window. Against the creme-colored wall hung a large painting, which he assumed was baroque, of an elegant woman, completely nude, swimming in a river covered in lilies at the surface.

“That’s...” he paused wondering if he could find the words to describe his awe. “Wow.” he finally said. He was speechless. He was amazed at the detail of the water, each little ripple defined in purposeful paint strokes. The girl looked a little bit like Ruby, not strikingly so, but she had that subtly wavy dark hair.

Of course, she could never be as beautiful as Ruby.

“Yeah,” she agreed, trying to dismiss it a bit. She smiled though, and thought to herself that Sam would be even more shocked if he knew it was the original, and had been professionally restored a decade ago. A gift from a particularly grateful, and wealthy, client. She had always been suspicious of the legality of her acquiring the artwork, but that bastard was in jail now anyway for tax evasion of all things. She didn’t really care.

“So,” she said out of the blue, turning around to face him, only inches separating their lips. “There’s something I wanna try.”

“Yeah?” he said, raising one eyebrow.

She whispered softly in his ear.

Sam looked a little surprised, but amused.

“Can’t say I’ve done that before but… sure,” he responded, shrugging his shoulders. “I’ll try anything once.”

“Great, cause I was hoping to stick burning candles up your asshole later,” Ruby joked, laughing and grabbing his ass playfully. “We should probably have a safe word or something. I don’t know.”

“How about Joffrey?” he suggested.

“Can’t think of anything less sexy,” Ruby said, smiling to confirm.

In a split second, he surprised her, putting a hand over her mouth, and adopting a stern face almost instantaneously.

“Now, you little slut, you’re gonna do whatever the fuck I tell you to do,” he commanded, his lips hovering above her ear, he paused adding to his dramatic takeover. “And if you don’t listen to me,” he added, chuckling in a deep and threatening voice that had her heart beating fast with excitement. “I’ll make sure you regret it.”

Sam was playing his part even better than she’d imagined in her wildest fantasies. She could be dominating, but with a man with a nature so sweet and caring, all she wanted was to see his dark side.

Ruby nodded obediently.

“Good,” he said in that same voice. “Now, on your knees.”

She did so, and looked back up at him with an innocent face of slight nervousness. It was all part of the act of course.

Sam unzipped his pants slowly; she could already see a bulge, and her heart was still racing like a derby horse, always excited to see his gorgeous cock and get her mouth all over it. When he finally removed his underwear, she was just staring with her mouth agape.

“Well?” he questioned impatiently.

Ruby reached up to grasp him, very lightly, and felt warm blood pumping fiercely through the veins of his length. Her mouth closed around his tip, and pulled away slowly, leaving a trail of spit that landed on her chin. She wiped it away before continuing, taking more in this time; her tongue stroked to skin at the bottom while her cheeks hollowed out. Precum leaked into her mouth as she sucked him off, making everything even wetter.

Sam loved seeing Ruby on her knees, practically worshipping him, completely subservient to his every command. He reached around to the back of her head, entangling his fingers in her hair and pushing himself deeper. Ruby made a sort of guttural surprised sound, and he suddenly wondered if he was actually hurting her. Shit, he really wasn’t good at this.

“Wait, wait, I’m really sorry if that was too much-”

“Shut up,” Ruby said assuringly, not accepting his apology, because he had no reason to in the first place. Did he forget they had established a safe word? And anyway, Ruby was sure Sam would never harm her. “You’re breaking character!”

Sam switched back immediately, grabbing her hair again, much harder.

“Did I ask you to stop?” he demanded, pulling her forward so her lips pressed against his erection.

Ruby wrapped her fingers around him, licking and moaning, bobbing her head up and down along his shaft. Knowing he had the green light, he maintained his grip in her hair, and pushed her deeper whenever she seemed to be pulling away.

“Take your shirt off.”

She released and pulled the dark blue tee over her head and onto the floor. All that covered her breasts was a black bra, so lacy and thin there was no way it was anything but impractical lingerie just for the occasion. Sam debated whether or not he wanted to get cum on it but he figured he didn’t want her to have to deal with cleaning up the nice fabric and everything. Her skin would do much more nicely.

“Bra too.”

Ruby sucked his tip, wet and sloppy, with one hand gripping him and the other unhooking her bra. How she did it with one hand, he had no idea, but it was so sexy he couldn’t focus on much else but the black lace falling from her shoulders and onto the floor.

Now Sam wanted to see if she could take all of him in. His hands roughly grabbed the hair at the base of her head and eased her forward till he was balls deep, and she hardly flinched. Ruby was trying hard to pull her focus to something else so she could suppress her gag reflex, not wanting to disappoint him.

His cock twitched a little, a sign he was probably close. Ruby decided he probably wanted to come on her rather than down her throat, she she slowly drew her mouth off him. She gave some attention to his balls, and base, kissing sloppily and moaning.

When he did reached his orgasm he just kind of lost it, and she gasped like her persona would, having never seen an ejaculating cock in her life. Ruby was kind of surprised Sam agreed to her little experiment- it was one of those cliché female fantasies that they were often too embarrassed to tell their man about. But around Sam, everything was easy, nothing felt awkward.

He watched the streams of white drip down her chest with satisfaction, and smiled, pulling his boxes back up.

“Go clean yourself. I’ll be waiting,” he said, his lips only centimeters from hers, as he ran a finger through a strand of her hair.

Ruby went to the bathroom and grabbed some paper towels, running water on them for a brief moment to get them wet. Sam flopped onto the bed as he watched her, admiring her firm little ass in her jeans, especially when the rest of her body was unclothed. He was still in the mood for that dynamic they had there- he liked it more than he’d care to admit. Being in control wasn’t usually his style, but now that he’d had a taste of it, he wasn’t going to stop.

He decided to be spontaneous, sneaking up on her from behind, and grabbing her by the waist. The feel of her soft, warm skin was nothing short of electrifying. With one hand he massaged one of her breasts, and with the other started unbuttoning her jeans. She moaned and gave in, her head falling back against his chest, as she felt two of his fingers rubbing her through the fabric of her underwear.

Sighs of Sam’s name slipped from her lips, but he raised his index finger to her lips.

"Shhh," he whispered, and she took the opportunity to take her pants off completely. Immediately he threw her over his shoulder roughly, catching her completely off guard. She let out a squeal of delight and beat her fists lightly against his chest, demanding he out her down.

He flatly refused. Until she said the word, she was his plaything and nothing more.

When he reached the bed, he tossed her onto her stomach, and she let out a little yelp, somewhere between surprised and frightfully excited. Before she could squirm away, he pushed her shoulders into the mattress; his fingers found the prize between her legs, and resumed rubbing her clit through the fabric. Ruby was panting, and it made him proud.

Sam realized only then he was totally hard again. He wanted to completely ravish her, rough and animalistic; hear her screams against his hand muffling her mouth. But he had to be patient.

His fingers hooked around one side of her panties, and ripped them off her in one swift motion. They were pretty flimsy, and she was too distracted to care.

Sam flipped her around onto her back, marveling at her naked body, his cock now totally rigid. His lips curled into a sly smile as he lightly grazed her clit with his middle finger, just barely teasing the sensitive nerves. Ruby gasped and her eyes fluttered.

"What, you like that?"

She nodded frantically, closing her eyes and arching her neck back into the mattress. He rubbed back and forth with a little more pressure.

“How about now?”

“Yes!” she exclaimed breathlessly. She tangled her fingers in his hair when he started making firm circles around the whole front part of her folds, and dove into her neck with his lips, sucking and biting a little at her skin, reminding Ruby he wasn’t gonna go easy on her. Her whole body was so overcome with frustration, with his taunting game she asked him to play; she pulled his mouth fiercely to hers and indulged.

Sam’s familiar taste was already like home to her; even the best orgasm in the world didn’t make her feel as close to him as a simple, passionate kiss.

He, however, wouldn't grant her that.

"You want me to fuck you? You're gonna have to beg."

She opened her mouth to speak but he brought attention back to the pool between her legs, slipping two fingers right into her.

"Just... God Sam, just go! Do it… so.. fucking hard... as hard as you-" she was panting so heavily she could hardly continue. "And... I want you to grab my ass and... spank me like..."

"Like the naughty little whore you are," Sam interjected, smiling as he finished her thought with the dirty talk she longed to hear. He added another finger and pumped his hand furiously against the front part of her walls, just along her G spot. Ruby could sense he was really involved in their fantasy; it was as much fun as it was ironically romantic.

With incredible force she pushed him off of her, forcing an end to the fingering. Her needy little hands found a tight grip around his girth.

“Stop it,” she begged. “I want you inside me… as deep as you can go… Now.”

He grabbed her by the jawline, staring into her pleading eyes with no mercy, pupils dilated, breaths heavy and low.

With his mouth so close to hers, she took the spontaneous opportunity to try to kiss him again; it was sloppy but unabashed. Their tongues moved together like an elaborate sword fight while Sam grabbed her ass roughly, then allowed his hands to wander freely, fondling each curve of her body.

It was a little too gentle for Ruby’s taste.

“Come on Sam,” she whispered in a sultry, breathy voice, in between the collision of their mouths. “Bend me over and give me the punishment I deserve.”

He didn’t wait a single second; he threw her forward, she stuck her ass in the air, and with obviously with only a small portion of the strength he had, smacked her right across her rear. She yelped with excitement.

“What a little whore, you like it dirty, huh?”

“Yes, yes!”

Sam smirked, even though Ruby couldn’t really see his face. He could see how wet she was, especially having been teased with his fingers earlier; he’d have her coming wildly the moment he pushed in.

“You want my cock? Cause I’m gonna fuck you so hard you won’t sit straight for weeks. You’ll be screaming so loud they’ll hear you in Manhattan.”

Ruby grinned to herself, unable to suppress the restless anticipation that consumed every nerve in her body, every brain cell. She heard him snatch a condom from her bedside table and put it on as hastily as he could, figuring he was just trying to get it over with. He'd pretend, for his character's sake, he was fucking her raw.

Muscular hands found her hipbones, and he gripped them tightly, before slamming into her, waiting to see her reaction before he continued. Ruby was practically purring. She dug her hands into the smooth fabric of her bedspread and her hands became fists when he pumped again. Sam wouldn't dare let her do anything but stay bent over and let him take her, and if she tried to do anything naughty he'd spank her again, less mercifully this time.

His pelvis was practically moving on his own, driven by overwhelming carnal desire, fueled by her complete submission, which he never thought he’d enjoy so much. She let out little yelps each time he plunged deeper and deeper, and moaned when he yanked her hair. Sam rode her like she was nothing but a filthy animal and she had never in her life found so much pleasure in being demeaned. A pulsing sensation was swelling in the walls of her cunt as he pounded again and again. She let out a piercing scream, completely unabashed, secretly wanting some neighbor to complain, just as a testament to how naughty she wanted to be.

"Wow, you just can't help it," he mused, chuckling darkly, when she let go. His hand muffled her as he was itching to earlier, silencing her wails. "Can't help but come taking my cock from behind? Well, you'll be coming again and again before I'm through with you." He gave her a good, hearty spank, and began thrusting into her with increasing speed.

Ruby moaned and panted with the synchronized rhythm of their bodies moving against each other. Sam untangled his fingers from her hair and moved under her body, kneading her breast in his hand, both for his own enjoyment and hers.

Before long she was coming again, and pushing him with her. He grunted with satisfaction as he spilled into the condom, holding her hips in place like he was filling her instead. He craved so much to know what it felt like to have nothing, not even a little latex layer, separating them, but in time of course… they weren’t irresponsible.

It went without saying that the whole charade was kind of over, Sam taking on a bit more of an affectionate way of holding her when she rode out the last rush of pleasure from orgasm.

“Fuck… Sam, that was the best…”

He smiled like a coy little boy. It made her feel a surge of endearment for him, his ability to switch from wild animal to gentle lover.

“I just kinda went with it, I don’t know…” he chuckled, interrupted by Ruby’s chaste kiss.

As their lips pulled apart, and they found an enamored gaze into each other’s eyes, Sam sat up to check his phone on the bedside next to him.

“Wow, it’s noon and I feel like we should probably fall asleep now.”

“You worked me hard, Sammy,” Ruby mewd in her signature sultry voice, although the effect was drowned out by her panting.  Running her pitter-pattering fingers down his chest, she noted how he was a little bit sweaty, and she couldn’t think of anything she liked more.

They stared into each other’s eyes, with nothing but burning adoration, for what seemed like hours, until Sam's phone buzzed. He rolled his eyes as he reached for it, and she sighed falling back onto the mattress with a long exhale. His eyes scanned the screen, and looked to his exhausted lover.

"Dean wants get together with some friends tonight... wanna come along?"

"I've heard great things about him," Ruby chuckled sarcastically. In all fairness, Sam's complaints were as harsh any younger brother's would be; numerous, but reasonable. She got the impression that at the end of the day, they had an exceptionally strong relationship.

"Ever played cards against humanity?"

…

“Ok, so… I’m gonna do it. I’m gonna text him,” Dean sighed, shaking his head like a piece of him wanted to resist. “He’s gonna call me such a fucking hypocrite but-”

He sat on his bed, holding the phone in front of him but not looking towards it, rubbing his temple with his other hand. It’s not that Sam would be upset to hear Dean found an actual relationship- he’d probably be thrilled. Anyone who knew Dean Winchester at all would be impressed, and if that person happened to be his brother, he’d never let him forget the days when actual romantic relationships disgusted him.

Cas rose up and sat next to Dean, extending an arm around his boyfriend’s shoulder. They had only been officially an item for a couple days, but they were so at ease with each other, just the way Sam talked about Ruby and their time spent together.

“He will know eventually. I suppose this is just a simple gathering, an introduction. Perhaps you don't need to tell him about us in a text, but rather in person?"

Dean looked into Cas' piercing blue eyes, pausing to think.

"Ya know, he has a girlfriend. They've been together like, a month or something, but it's kinda serious. And this could be an opportunity to finally meet this woman with Sam's balls in her purse."

"Yes," Cas responded, oddly solemnly. "What's her name?"

"Ruby."

"That's a beautiful name," he said, smiling.

Dean raised his eyebrows, and took a symbolic deep breath, as if for some reason, inviting his brother to fuck around at his apartment was the hardest thing he'd ever had to do. He started typing rapidly, and hit send.

"By the way Dean, I think you received a package today," Cas informed him. Dean just chuckled at the innuendo.

"Did I?" he said with piqued interest, running an eager hand against Cas's crotch.

"I wasn't referring to..." Dean cut him off with a fierce kiss.

"Ya I know, an actual package," he admitted. He made his way to the door, and read the label of the box.

"Ah, finally!"

"What is it?"

"Ever played cards against humanity?"

...

Sam and Ruby showed up at Dean's 10 minutes late, with messy, slightly damp hair, as if that raised no suspicion. His hands glanced down at their interlocked hands, arms practically intertwined as Ruby leaned against his brother's shoulder.

"Sorry!" Ruby chuckled apologetically, pausing before adding, "So, you're Dean?"

"The one and only," he responded with a coy smirk.

"Wow... you look nothing alike," she remarked, glancing back and forth at their faces. Dean shrugged.

"Poor Sammy got the shallow end of the gene pool."

"Then I guess that puts you in the kiddie pool, huh?" Sam could hardly contain himself at his girlfriend's wit. He really could've used her help in the arguments he'd had with Dean as teenagers.

A blonde head popped out from around the corner, recognizing the voices entering the apartment.

"Jo!" Sam exclaimed, conversation cutting off there.

“Hey guys!” she responded, hugging both of the arriving guests. “So I’m assuming Dean hasn’t spilled the beans yet…”

Sam looked at Dean with a raised eyebrow, his brother chuckling nervously in response. He was gonna kill Jo, and at the same time, he was sort of grateful she was nudging him to get his big confession out of the way.

“Yeah, so… um, this is Cas,” he said simply, motioning for Cas to come from around the corner to say hi.

“Castiel Novak.” He extended his hand to Sam and Ruby each.

Once Sam could get past the irony that Dean was now in a committed relationship as well, with a man as solemn as Cas, and Ruby was done being thoroughly entertained by the spectacle, they got the game going.

Dean’s boyfriend was his opposite in so many ways. Kind of clueless to pop culture and the rude jokes in cards against humanity, a bit bashful, but he brought out a more genuinely sensitive side of Dean. That made Sam happy.

“Alright, alright, I’m judge!” Ruby exclaimed as she picked a black card from the stack, and flipped it right side up to read the prompt.

“I do not know with what weapons World War 3 will be fought, but World War 4 will be fought with _blank_.”

Jo chuckled to herself smugly, eyeing her cards with pride. Sam smirked a little, Dean put one down alarmingly quickly, and Castiel seemed to be rereading each of his one at a time, like he wasn’t sure what to make of the dry humor.

Once everyone had put one down, she took her time reading them, entertaining the other players.

“We have… poorly-timed holocaust jokes, elf cum, flying robots that kill people, and gloryholes.”

Everyone snickered.

“Okay, so… flying robots is out, that’s not creative at all.”

“But it is the only logical response," Cas protested. "As, likely, flying autons will be the most prominent method of warfare of the future,” Dean gave him a look communicating, for the millionth time, the game was not at all meant to be taken seriously. "I do not understand this,” Cas sighed, putting his cards down defeatedly.

Ruby took several more seconds to consider, before choosing poorly-timed holocaust jokes. Jo cackled victoriously as she claimed yet another black card to add to her pile. The next round was beginning, Sam’s turn at judging, when Ruby felt her phone buzz in her pocket. She ignored it, picking up and fanning her cards in front of her to review her options, but it vibrated persistently. The screen displayed an unfamiliar number, only four digits, which was strange. Fearful it was a threat, she knew she had to answer.

“Sorry guys, I’ll be right back.”

Sam could sense the worry in her voice, and looked at her, concerned, silently offering whatever help she might need. Ruby smiled to brush it off.

When she was locked into the bathroom, she tapped the green icon firmly to answer the call.

“What do you want.”

It wasn’t punctuated like a question. It was a clear demand.

“I have information,” responded an alarmingly processed voice, making the true one of the speaker completely unintelligible. Whoever was on the other end wanted to be taken seriously, without revealing their identity.

“What. Do you. Want,” Ruby reiterated. Asking their name or affiliation would be pointless.

“Don’t go home. You need to get out of town, and fast,” the voice warned expressionlessly.

She wanted to pose some question, some rebuttal that would discredit the anonymous tip, but she had none. Something told her it was legit.

“If you really care about me so much, why don’t you give me something to let me know this isn’t complete bullshit?”

“I work for Lilith Carter. Seen files I shouldn’t have. I’m just trying to do the right thing. I'm on your side.”

Ruby sighed harshly, and let her body fall against the wall.

“So what is Lilith planning anyway?”

“Awful things, but I can’t figure out anything specific. She has someone with the codename ‘Knight of Hell’ doing her bidding.” The voice paused, before hastily adding, “I need to go. Do not attempt to contact me. If I contact you, I’ll use the codename HG.”

It hung up.

…

The party was already winding down when Ruby left the bathroom. Jo easily won with a whopping 14 cards to runner up Sam’s 10. Castiel won 3, but didn’t seem terribly discouraged. Dean insisted his boyfriend would get the hang of it next time.

Ruby and Sam made their way out of the building, heading to Sam’s place only four blocks from Dean’s, and he could tell something wasn’t right with her. They walked hand in hand at an average pace, but Ruby’s breathing was irregular, and her movements brisk. Sam stopped for a minute by the corner of a worn down brick building.

“Are you ok?”

“Yeah, I am, just…” she paused, her thoughts spinning, trying to devise something.

“Do you want to go on a vacation or something? I’ve never actually been to Hawaii, and I’ll do anything to get out of this shitty weather-”

“That'a why you’re upset? Cause it’s winter in New York?” Sam asked skeptically.

She sighed. So many times she had come to a moment where confessing everything she hid would’ve been so convenient. This was one.

Ruby looked at him long and hard before continuing. “No, no… whatever, I’m being stupid, let’s head back,” she said hastily.

Sam smiled sweetly. Dilated pupils in the dim light only added to the puppy effect. It was easy to forget this was the man she spent most of her day just having rough sex with.

He pressed a soft kiss against her shivering lips, comforting her with infectious warmth she craved in times of stress. She had no plan, but whatever came, she would put Sam’s safety before anything, even if he never wanted to see her again- even if she got killed.

At that exact moment, Ruby felt cold metal against the back of her neck. All sense of comfort shattered in an instant. She heard Sam inhale sharply, and she realized he had a gun against him too.

A cool, collected, almost elegant female voice spoke in their ears.

"Let's take a walk, shall we?”

 

**Notes for the Chapter:**

> Hope you guys enjoyed this chapter! I apologize for taking so long. (like a month??? gosh I suck) But I am sUPER DI DUPER excited for what's coming up!  
> Pleeeeease comment, kudos and bookmark! Let me know what you're enjoying, any suggestions, any theories, whatever you want! It makes me so happy :)  
> As usual, for updates on this fic, track #eots sr (eye of the storm sam ruby) on tumblr. Volunteer to be a beta while you're at it!  
> Thanks guys, you rock!!


	9. Ruby Red

**Notes for the Chapter:**

>  **TRIGGER WARNING:** THIS CHAPTER CONTAINS, ALTHOUGH NOT GRAPHICALLY, DESCRIPTIONS OF PHYSICAL VIOLENCE AND RECOUNTED DOMESTIC VIOLENCE.

With guns pressed into their shivering skin, Sam and Ruby found themselves paralyzed. The air in their lungs suddenly froze.

"Are you two deaf? Walk."

Their feet shuffled on the damp pavement. Heading towards the darkness, the smell of dumpsters crept into their noses. They heard their attacker let out a dark chuckle.

"Nice to finally meet you kids," she began, rotating so they could see her face, put keeping her loaded guns inches from them. "Unfortunately, our acquaintance will be brief."

The woman was strikingly elegant, from what they could see by the dimmed street lights. She had a strong nose, a wide lipped smile painted bright scarlet, and what caught Ruby's eye most was vibrant red hair. Was this the woman who had been spying on her?

"Put the guns down," Sam began uneasily. "And we'll give you our money."

Ruby knew how to keep her cool under threat. She had trained herself for the past decade. But with Sam's trembling body next to her, so fearful even in his remarkably built stature, it wasn’t so easy. He had never had to face anything like this; he didn't deserve to. In a single moment, she felt a burning self-hatred surge through her body, picturing Sam lying bloody on the desecrated alleyway ground, all because she walked into his life, lugging along a lifetime of baggage.

"How generous, pretty boy. But that's not what I'm after."

The woman suddenly socked Sam in the nose, with an incredible force he never would've expected, causing him to trip backwards. He clutched his face, streams of blood violently springing from in between his fingers. Ruby couldn't understand what she was trying to do, as freeing Sam from her gun only gave both of them an opportunity to bolt. This bitch was clearly acting on Lilith's orders, but which of them Lilith wanted dead, Ruby didn't know.

She heard Sam gasp as he lowered his hands from his nose, still gushing blood. He watched the woman grab her and press a knife against her throat.

"Make one move," she threatened. "And watch your little Ruby get her throat sliced wide open."

Sam looked desperately to Ruby's eyes, as if asking, Do you know what this is? How could she know your name? She could hardly breathe, but she tried to say, I'm so sorry.

"Sam," she choked, eyes tearing a little, even as she tried to maintain her strength. "Get out of here. It's not you she wants."

He stood firm, shaking his head slowly.

"What do you want from us?" he asked in desperation, addressing the woman.. "If you just want to kill someone, take me, just please... let her go. She’s innocent, she’s done nothing to hurt you."

The woman cackled. Lilith had told her Sam would be a self-sacrificing little sap.  Driving a knife through his head would be a treat. However, her cousin had given excruciatingly specific orders, and Abaddon wasn't about to let her sweet deal crumble over failing to get rid of the little pest.

"How adorable," she said with a condescending smile, watching with joy as Sam's face turned to an expression desperately masking absolute mortification. "Innocent little flower, this one. Remind me Ruby, when did you start fucking your crack dealer? 15, maybe 16?” She paused, eager to see how Ruby would react.

“Does Sammy here know anything real about you? All the lives you’ve ruined, the people who suffered so you could escape your shitty little life. But of course, you would never let your precious Romeo know the truth... couldn't bear the thought of losing the one person who ever gave a fuck about you, could you, Emily?”

Ruby had practically lost consciousness. Not physically, but her entire being was prepared for death, accepting that her life was always going to end like this. A quick action plan played out in her expertly-trained mind, as was her instinct; a solid kick to the crotch, with about a 1/4 second window to grip and snap her wrist, and deter her with a punch to the jaw, or nose, whichever was more convenient. Within about 1/2 of a second after that, she’d whip the guns from her, pin her down with her own knife, and do whatever the situation called for. Ruby quickly estimated about a 90% it would all work out. Any old day, she’d take anything above 30%- but now, it wasn’t her life she was risking. One slip up, and a bullet would go through Sam’s head.

"Then again, you’ve probably given him 4 different strains of herpes by now,” the woman began again. “He’s got to have some pretty low standards, huh?" She cackled and made a small cut with the knife, watching blood drip down Ruby’s neck, and smiling with sick glee. Sam glared at her, clearly trying to push away any thoughts considering the validity of what this woman was saying.

"Well, anyway, Lilith sends her regards."

For someone who had been through as many near-death experiences as Ruby had, she really should've seen the signs of the events that transpired next, in split seconds, in a single beat of her racing heart. Vengeful monologues were a red flag for a killer who didn't kill for a living. Overconfidence is what sets the adrenaline-rich veins of the threatened aflame.

Blade tore through flesh. Blood gushed.

The woman crumbled to the ground.

Ruby looked up, so overwhelmed with conflicting emotion, she could hardly speak. Sam gripped his dripping pocket knife before him, breathing harshly through his mouth as he processed what he had done. The body at his feet lay gasping, until her mouth overflowed with blood, and she could no longer.

Ruby looked up to Sam wordlessly. He stayed frozen as a statue, as if she wasn't even there.

"I'm... so sorry," she said, approaching him and falling into his arms, feeling tears come on.

"Who was she?"

Ruby stayed still, trying to memorize the feeling of being close to him; the warmth and the smell he always had, a little sweat and a little musky. She wouldn’t have it for much longer.

“All that stuff. Please tell me she was just making it up,” he questioned again, more harshly, and pulled a crumbling Ruby off of him.

“Honestly, I have no idea who she was!” She wasn’t lying, but it had come to a point where she knew there wasn’t a way out. Sam would have to know the truth. In a completely cliche way, her feelings no longer mattered, all she wanted was for him to be safe, to find someone to love him the way he deserved, who didn’t lie to him and put his life in danger.

“I had- really rough teenager years. I got into some… drugs, sketchy crowds,” she sighed, a tear finally releasing from the corner of her eye. “I got out, I never looked back, and… I can guarantee I don’t have herpes.”

"...and Lilith..."

"I..."

Sam kept staring at her like he couldn’t decide if he was angry at her or relieved they made it out alive. In a split second he made his decision, pulling her into an embrace so tight, like he was holding onto her for dear life, for his sanity.

“We should call 911.”

She shook her head, and placed her hand on his pocket as he began to reach for his phone.

“No… look, we need to get out… we can call 911 from your place. We don’t know who else is here.” She paused as her eyes welled up a bit, and she gently cupped the side of his face. “Please, Sam…”

He nodded, closed his knife, and took her hand. They crept wordlessly out of the alley, fingers interlocked so tightly they could feel each other's pulses. Ruby’s mind was finally clear enough to think back to the red hair- it just wasn’t right. Her spy’s was a bit lighter, figure a bit smaller in stature. She questioned if this whole Lilith thing was much more complex than she could’ve expected. Fear for Sam’s safety was consuming her. She decided, in that moment, she would put nothing, not even her life, before his.

As they reached the lobby, Sam paused. He glanced at their surroundings; no one seemed to be following them.

“We should stay in public. Have the front desk call 911.”

Up until that point, Ruby had desperately wanted to avoid any police interaction. With the stakes so high, she somehow forgot that she could talk her way out of just about anything, let alone some local police interview. Chances were they would successfully identify the woman who attacked them, but it’s not as if Lilith would come forward about hiring her- and considering all the guns she had with her, Sam’s self-defense story would probably be believed. He had a spotless record, a wealthy, well-known family, no way would he go down for something like this. If he did, she’d turn herself in for every crime she’d ever committed.

The two of them approached the pristine marble desk, where a man in a suit sat at his computer. Sam’s hands shook as he placed them on the counter. It finally began to sink in- he’d killed someone. She would’ve killed Ruby, maybe him too, if he hadn’t, but still, he could tell this was a night that would stay with him his whole life. The knife in his pocket felt like it was burning against his skin, taunting him for what he had done.

“How can I help you, sir?” the man asked as his eyes finally found Sam waiting.

“Uh… we need you to call 911. We were attacked two blocks down, in the alley behind…” he was clearly not thinking clearly enough to give any more useful in formation. “...some building, I don’t know.”

Ruby squeezed his hand and looked at him, compassionate eyes assuring him wordlessly that he was ok, and she loved him.

“Oh, gosh, I’m so sorry- why don’t you come sit down in the back and wait. We don’t want to cause a scene,” the man responded, shaken out of his apparent boredom. “Do you have any idea where they went?” he added.

Sam opened his mouth, but stopped, all the air evacuating his lungs.

“We’d rather not talk about it,” Ruby responded firmly, and the two of them sat down at some chairs next to a vending machine.

…

They spent what seemed like days at the police station. She had a purse full of fake identification, some completely unnecessary, but she had become a bit of a collector over the years. Why not carry a PADI scuba certification card with the name Ruby Masters on it? She got bored one weekend Key West. Just another coping strategy, she assumed, but it wasn’t something she wanted to ponder right at that moment.

Sam’s head was on her lap, his back bent at an awkward angle to compensate for his height. Her fingertips grazed his hair, soft even when a little sweaty. Ruby always found herself admiring the way his lips parted ever so slightly when he slept, so tragically innocent despite everything he’d seen… he was the man who loved her so much he’d do anything to protect her. For two months, she returned the favor with a lie that was sure to tear her whole life apart.

“Hey,” said a police officer, approaching them. She wasn’t the one Ruby and Sam spoke to before– Ruby’s eyes glanced at her badge. In embossed silver letters, it read, “Sheriff Mills.” Kind of sounded familiar.

“We’ve identified her. Abaddon Sands, 34, one of the wealthiest socialites in the area,” she explained, handing Ruby a file. “Have to say, not our typical profile for back alley murder attempts, but you never know with people these days.” The sheriff gave her a moment to get a good look at the basic information on the page.

“Ring any bells?”

Ruby shook her head, and handed it back.

She smiled sympathetically at Ruby, almost touched by the way she cradled Sam, so lovingly despite everything. He was lucky to have her.

“As for the case on her death- we might have to take it to court depending on what the forensics say, but I guarantee he’ll come out fine,” she added. “Is there… anything we can do for you guys? Do you have a place to stay? We can’t have you in the apartment until we’re sure everything’s safe.”

“We’re fine,” Ruby responded, genuinely grateful. “Thank you so much, for everything.”

“Well, that’s why I joined the force. To fight for the good people who’ve been through bad stuff.”

It hit Ruby then- Mills. It was the officer she bugged when she was first seeing Sam. This kind, understanding woman, who wanted nothing more than make the world a better place- another pang of guilt to add to her long list of ways she put people in danger for her own gain.

The worst of them all slept like a baby in her lap.

…

“Ms. Carter… how would you describe your relationship with your cousin?”

Lilith was incredibly uncomfortable in the interrogation room, but she kept her cool, reminding herself that worming her way out of suspicion would be a piece of cake. She pursed her perfectly glossed lips, and looked to the side, as if she was struggling to find words to explain Abaddon.

“We weren’t particularly close. She was nice I guess, but, always a little… off, ya know?”

The sheriff looked steadily at Lilith, unsatisfied with her vague reply.

"Was she violent as a child? Socially awkward?"

"Both, I suppose," she sighed, trying to convey a sense of pity for her. "Sometimes I saw her sitting in her garden alone, drawing pictures of herself holding a knife and a bloody cat. She always hated Sunshine, that poor thing..." Lilith sniffled, and Sheriff Mills passed her a tissue box.

Truth be told, she almost got a thrill from making up bullshit about Abaddon. It's not like anyone could say otherwise- Cain hadn’t paid attention to her in her youth, as he was already 10 when she was born. Her parents were dead, as were her grandparents, and Henry Sands, the stupid fool... he had no evidence to argue against Lilith's word either.

"Did she ever show physical aggression towards–" the sheriff paused and glanced at her notes– "Sunshine? Or other animals?"

"Now that I think about it... she chased him around the house, and would laugh when she grabbed him, pretty forcefully for an eight year old. Her parents didn't stop her, they were too busy with their careers and parties. I guess... it sorts of makes sense that being neglected affected her life. I never thought she'd try to kill people, but then again- no one really knows a psychopath til they do something like this."

She watched as more notes were taken, and sniffled again for some added effect.

"Gosh, my family is so broken... I'm sorry, I don't want to get off track, it's just, I think I need some time to process it, so if I could come back later, possibly–"

"Just one more question," Sheriff Mills interrupted, seeming apologetic despite knowing that she hadn't gotten to the good stuff yet.

"We have gone through her cell phone and noticed that her last call was from a private number. We're still working on tracing it so we can find out whoever that was. But would you happen to have any knowledge of who the caller might have been?"

Lilith shrugged, sitting uneasily as to hopefully tell her interviewer she didn't really want to continue. A little spark of panic incited in her- nothing she couldn't handle, but she had to take care of some damage control the moment she could get out of this police station. The very environment made her uncomfortable- everything smelled like cheap coffee, all the officers save Mills seemed like pretty apathetic tools, and some shabbily dressed, handcuffed teenager waiting outside smelled heavily of marijuana.

"I hardly know what that means. I'm no tech wizard, otherwise I wouldn't need secretaries!" she chuckled. "But no, I haven't the faintest idea."

"I see. We think it's possible that it wasn't a random encounter, that someone wanted Ms. Sands to target those specific individuals. It just so happens that one was Sam Winchester, son of Senator John Winchester, and as you undoubtedly know, the presidential candidate your boss, Senator Lucifer, is facing in his campaign."

She left it at that, no question, waiting for a reaction.

"Like I said, I simply have no idea. Mark, myself, and the rest of our staff- we wish no ill on John or his family. When politics aren't concerned, the two are actually very friendly." She paused, almost feeling insulted at the accusation, when it was completely logical, well– true. "Mark stands for old American values, honesty and integrity, and I can say without the slightest bit of doubt, he would never authorize some heinous plot to hurt John like this. However, like all politicians, he has his fair share of radical supporters- I've dealt with them myself. It makes my heart ache saying this, but I suppose there might be someone who would go this far. Mark would be disgusted to know that, if it were indeed the case. As would I," she finished firmly. This had been an Oscar winning interrogation, she thought to herself.

After scribbling the last of her notes, the sheriff dismissed her. Lilith grabbed her Fendi purse, and walked, poised but oddly hastily, out the door.

Alone in the interrogation room, Jody kicked back her feet, placing them casually on the table. She scanned her notes, and tossed them to the side. She knew a liar when she saw one, and she had evidence to back it up.

They wouldn't have brought that woman in to be interviewed had they not done some research on her first. Cousins were rarely the first people the questioned, but this one, she was suspicious. Flipping through the file, she saw Lilith's college record- multiple advanced classes in computer studies and digital media.

"No tech wizard, my ass," she chuckled to herself.

As she made her way to the main office, she stopped at her desk to make a phone call. One the very first page of Lilith Carter's file, bolded at the top, was a number. She quickly dialed it.

"Lilith Carter's office, how may I help you?" a bright, chirpy voice asked.

"You're Charlie Bradbury, am I correct?"

The woman on the other end paused, clearly a bit confused, as she had never received a personal question on this line.

"This call isn't going to be recorded, we've ensured that. My name is Jody Mills, sheriff of the NYPD. We have some questions about your boss."

…

Staying at Dean’s place was incredibly awkward, to say the least.

For one, Sam could never quite look anyone in the eye, Ruby especially. She insisted he could skip his classes, but he needed a routine distraction so he didn't have to remember the blood-stained knife that haunted him, day and night. When the two of them were alone, she curled up against his chest, hoping some intimacy would make him feel safe. He didn't stop her, but he lay still, never pulling her as close as he used to.

Dean and Cas did a decent job giving them their space- Sam was unwilling to give them all the details of what had happened, and maybe if he had Dean especially would be a bit more sensitive. Their first night he asked if he needed to soundproof the walls or anything. Not like he could; they were stuck on a worn out blow up mattress in the living room. One night they heard the bed shaking violently through the rather thin wall separating Dean's room from their temporary one. Ruby would never admit it, but- it was kind of turning her on, the thought of two guys pounding each other only several feet away.

"God I can't wait to leave," Sam mumbled, trying desperately to not think about what his brother and his boyfriend were doing.

"So why don't we?" Ruby asked, propping herself up, and running her thumb along his hairline affectionately. "The police said it was ok."

He didn't really respond. She took it upon herself to get something out of him.

"Until then," she began in a sultry whisper. "How about we distract ourselves? Give Dean and Cas a dose of their own medicine?"

"No... look, not now, I just want to sleep."

Ignoring what she assumed was a decline that could be very easily changed, she dove into the crook of his neck, sucking against the skin below his jaw, and creeping her fingers into his underwear.

Sam moved her hand away, and really looked her directly in the eye for the first time in what seemed like ages. Her eyes were wide, alarmed, and he felt awful. He wanted nothing more than to make love and indulge in the bliss he so loved, but something inside him just wasn't there. His love for her was as strong as always, but he almost felt like she didn't deserve him- in the end, he was a killer, and she didn't seem to want it to change their relationship at all.

"When will you get it? I'm not like you, I can't just go back to normal, I can hardly look at you feeling everything all over again. Doesn't it scare you? Your boyfriend– sliced someone's throat open–" he was choking on his words, feeling now, more than ever, like an absolute monster.

"...and I still love him as much as I did the first time I told him so," Ruby interjected. Sam sighed, not feeling like there was anything more he could really say. A sudden burst of courage came from somewhere within her- and she spoke.

“I- when Abaddon said Emily-” she began unsteadily, not knowing how to say what she wanted desperately to blurt out. “That’s my real name. Emily Milton. I don’t know she knew, I mean, I’ve been using Ruby since I was 17.”

He was listening patiently, his eyes showing a sense of forgiveness for things she hadn’t even told him- it broke her heart how unconditional his love was, or so he thought.

“I was done with foster homes when I was 15. They were awful and when they separated Anna and me, which they promised they’d never do- I went AWOL. So… yeah, I ended up 16, with a 24 year old boyfriend, and he hooked me up with the drugs I wanted. Props to Abaddon for somehow knowing that,” she said, shrugging sadly, voice shaky. It was the first time in years she recounted those days to… anyone, really.

“Ruby, you are not the one to be ashamed, what he was doing was completely wrong, I mean like, supplying drugs, statutory rape wrong,” he assured her, placing his consoling hand on hers. “Please tell me he didn’t… really hurt you.”

She exhaled slowly as she thought about it.

“Not at first. He was sweet, he got me into clubs and I pretty much forgot how unhappy I was. I was completely broke, and eventually he started expecting me to find some way to pay him for everything he’d given me. One night, in his apartment, I told him I was leaving, but he clocked me over the head with a beer bottle, and I don’t even really remember much, not in detail… but I can see him, pushing me down and tell me he’d beat me to death if I didn’t find a way to get him all the money I owed,” she was tearing up a little, but she had long ago come to a place of acceptance.

“What some guys do… it makes me sick,” he shook his head, disgusted by the thought of anyone hurting Ruby.

“I ran onto the balcony, and somewhere along the way… I pushed him off. I don’t know how, but I killed him, and I spent hours telling the police it was an accident. They knew he was trying to beat me up, I didn’t argue with that. I needed to stay out of the police radar though, considering they were bound to find drugs somewhere in his apartment, so the moment they left, I ran away again. They opened a missing person case, so I dyed my hair a shade called Ruby red- that’s the story there. Who knows if they’ve closed it yet, but hey, 10 years and they still haven’t found me. The only person I ever told was Anna. I hoped she would care about me enough to not say anything to the police, and she didn’t, but only because she didn’t care at all. Of course she wouldn’t want anything to do with a sister who abandoned her before she even finished 5th grade.”

Sam broke their eye contact as he started trying to take it all in. He was in law school, shouldn’t he care that she deliberately ran away from the police? Yet, he found himself realizing- he didn’t blame her. For anything. Not in the least.

“How’d you get so rich? Please tell me didn’t rob any banks,” he chuckled, realizing it still came off kind of wrong. “I- I’m kidding, sorry.”

“It’s ok. I just needed to tell you, cause first thing tomorrow I’m going to Sheriff Mills, and I’m turning myself in. I was ok on my own, but now I brought you into this mess, and I love you more than I’ve loved anyone else in my life…” her voice was cracking as real tears came on. “I was so selfish to put you in danger, Sam.”

He pulled her in as tightly as he could. He still loved her as fiercely as always, and nothing came before her, not even the law. She didn’t belong in jail. He wasn’t going to let that happen.

“No, Ruby, don’t you dare. I could never be angry at you- everything you’ve been through, you keep going, and no one with a heart would punish you for that.”

He kissed her hair, his hand cradling her head weaving his fingers through it. After several minutes of a wordless, but deeply intimate, embrace, he lay her down at his side. He saw a tear on her cheek, and he wiped it away, whispering soft declarations of love, over and over, until he fell asleep.

Meanwhile, she couldn’t take her eyes off the ceiling. She told him nearly the whole truth, and yet, left out the most crucial part. Her selfishness overpowered her, and she felt no relief.

Whenever it seemed like the moment was approaching, to tell him the real truth, the truth about why she came into his life in the first place, she found some reason to make an excuse not to. Her heart felt like it was made of lead when she pictured a lifeless body at her feet, bloody and broken– not Abaddon's, but Sam's. Ruby would rather die than witness that horror.

**Notes for the Chapter:**

> Thank you so much for reading! It's a pretty heartbreaking chapter, I know, but... not gonna lie... it's only gonna get more intense. I hope you're enjoying the ride though, cause I sure am.
> 
> Please please pleeeeeease leave comments! I want to hear what you think, any predictions, any suggestions, limericks about how great my writing is... :)


	10. White Flag

**Notes for the Chapter:**

> Lemme know what you think guys! Leave kudos and comments, as usual. :)
> 
> Things are getting pretty intense... hope you enjoy reading about fictional characters getting their lives torn apart as much as I love writing it!

When Sam and Ruby finally got to return to his place, their faces lit up at the sheer sight of an actual somewhat organized apartment, free of random beer bottles and the occasional porn DVD under the sofa. Maybe there was one at this place, more likely than not- if Ruby found it, she’d make him watch it with her.

Sam plopped onto his couch, the one they first had sex on, and it made her kind of stupidly sentimental. They had made it _this_ far. She followed him and jumped onto his lap.

Ruby’s phone buzzed, barely audibly, from somewhere in the room- she couldn't quite locate where by the humming sound alone. She drowned out the distraction to settle back into Sam's warm body, but it was persistent. As gently and discreetly as she could, she moved his arm from her waist, and tiptoed to her purse.

The screen read a missed call from an unknown number. She assumed it was HG. A sudden surge of panic swept through her as she pressed the phone to her ear and listened to the dialing

“Hello?”

“Code red. Get out of town, take Sam with you,” the familiar digitally manufactured voice spoke. Even through the heavily distorted monotone of the voice, Ruby could sense the speaker was anxious. She looked to Sam and flashed him an expression, wordlessly saying she needed some privacy to take this call, and secluded herself in the bathroom.

“Look,” she responded, once she was out of Sam’s hearing range, somewhat in denial of the still-present danger she faced. “I’m not trusting you just ‘cause you gave me one anonymous tip that nearly got me killed anyway, so, thanks. I can’t trust fucking anyone right now. So you’d better give me some little shred of a reason to believe you aren’t just another one of Lilith’s pawns.”

There was a pause, and a bit of white noise. It spoke again.

“Here, this is it. My real voice. Happy?”

It wasn’t the mysterious, gruff male voice she sort of expected it to be- it was a woman. For some unexplainable reason, Ruby felt like maybe she had been too harsh, expecting HG to be some creep. The anonymous tipper on the other end sounded more nervous than anything.

“And HG? What does that stand for?” Ruby asked, genuinely curious, now that she had a bit more confidence in her mysterious guardian.

“Um… Hermione Granger,” the woman said, chuckling bashfully. “Kind of my hero, I guess.”

“Oh,” Ruby responded. “Fine, I’ll listen, but everything’s with a grain of salt, so don’t think you can still pull something over on me.” She paused, taking a deep breath. “What is Lilith plotting?”

“Worse than you've ever imagined she was capable of. She’s got some thug with her, a real killer-” White noise started drowning out the voice again.

“Whatever you do, don’t-”

It cut off there, and she was left with nothing but beeping.

Ruby’s heart was pounding; things were getting even more serious- Lilith wasn’t going to back down, not after plan A failed when Sam killed Abaddon.

To her relief, her phone buzzed once more, the same number displayed on the screen.

“What? What shouldn’t I-” Ruby began the moment she picked up, her resolve to seem calm and collected quickly fading. She had dealt with every brand of scheming, vengeful psychopaths her world had to offer, but never like this, never on such a personal level.

A cold female voice cackled on the other end. _Oh God, no…_ Ruby thought. _Please no._

“Long time, no see,” Lilith began, voiced honeyed and mockingly casual. “Or- speak, I guess. Glad to have had Charlie keeping you up to speed, but, well, she’s deterred at the moment.”

Ruby swallowed, and convinced herself this was nothing.

“Right, sabotage your secretary while the police are already hot on your trail, that won’t raise any red flags.”

“Oh please,” Lilith scoffed. “She’s not as stupid as you are, at least in regards to protecting phone calls. I don’t know where she is, I don’t really give a fuck, I’ve got lots of people handling that for me.”

She paused and sighed, undoubtedly trying to exercise her intimidate, emphasize her superiority.

“That’s the difference between the two of us; I’ve got people, I’ve got real money and power, and you think you’re some kind of lone wolf underdog who’s going to save the day in the name of love! Like a little Disney critter. You’re no one, you always have been, and the part that really gets me is you just don’t know your place. As far as I’m concerned, you’re barely even relevant to this anymore. We’ve got file cabinets full of back-up plans.”

“Yet you still took the time to personally send your cousin to murder me. I’m touched,” Ruby snapped.

“You’ve got guts, I wouldn’t deny that. You always have been a cockroach I can never seem to squish,” she retorted, sickly sweetness of her voice fading with each word she spoke, making way for a more aggressive tone. “On some level, I respect that. So, I think we should compromise, don’t you?”

Lilith paused, but Ruby didn’t say anything. She was terrified, but whatever deal this woman was going to propose, she knew full well she might have no choice but to accept. Lilith must’ve been smiling with glee, knowing she had finally broken her, but Ruby was simply too exhausted to care.

“I want to sweep this whole Abaddon thing under the rug. You want Sam’s safety. So let’s keep it simple; you be my scapegoat, I’ll expose you for every crime you’ve ever committed, along with hiring Abaddon to kill Sam, and we’ll leave his family alone. Granted, prince charming will hate you till the day he dies, but he’ll live. Maybe find a woman he can actually have a future with.”

“What, so you’re just going to give up the entire campaign? How does this benefit you at all?”

“Oh, Ruby,” Lilith began, condescendingly as usual. “I have priorities, and at this point, I need to cover my tracks with this whole trainwreck of a plan. It was poorly conceived from the start, and I apologize for that, but what’s done is done. Luckily, Lucifer’s been gaining on Winchester in the last month, by about 6.5% of Republican voters, and primaries start in only two weeks. My job as campaign manager has been a huge success. All that’s left to do is clean up your mess.”

Ruby began to say something, but Lilith quickly interrupted. There was a point she needed to be getting across, no matter how long she had to drill it into Ruby’s skull.

“Let me be excruciatingly clear- it’s not really a two way street. Your refusal won’t hurt me, but it sure will hurt Sammy, in every way you could possibly imagine.” She chuckled darkly before adding, “Don’t think for a second I’m beneath that sort of non-traditional motivation tactic. I’ll have my buddies beating him to a pulp till he’s begging for death, screaming your name, only to learn you were the one who got him there. Just let that image sit with you.”

A deep breath, and Ruby knew there was no decision to be made. She had lost. She was always going to lose. Worst of all, Lilith had achieved full victory; it wasn’t about Sam, not for the last two months. She knew the woman craved for Ruby’s surrender, waiting patiently to hear how weak and childish even the most reputable private agent was deep down.

Lilith was so fucking right.

Ruby pictured herself rotting in a jail cell, and it hardly phased her, because out there in the world, Sam Winchester had long ago forgotten about his traitor of a girlfriend. He had a wife and kids and a normal life. And love. The one courageous thing she could do at this point was to give him that.

“I accept.”

She could sense Lilith’s satisfied smile on the other end.

“Good girl. I’m glad we can see eye to eye on something, and to thank you for your cooperation, I’ll keep this simple; at 6 AM, a black SUV will meet you at the stairs of the lowest level parking garage of my office building. From there, I’ll disclose the rest. Understood?”

“Yes,” Ruby replied somberly.

“I have my ways to make my ‘incidental discovery’ of your role in the plots preceding my cousin’s death seem genuine, so don’t fret. The more easily we can prove your guilt, the better this will be for the both of us. So bring any sort of additional evidence of your guilt in the crimes you did commit- all the fraud, sniper training, owning a closet of nothing but black leather catwoman outfits, whatever else you think might be useful. You get one more night with precious Sammy, and if I were you, I’d keep this whole agenda to myself. Fuck him till he’s spent, leave at the crack of dawn, and never look back.”

The conversation was dragging on, and Ruby suspected Lilith was just enjoying herself too much. There was no use in trying to work around her again, not with the safety of the man she loved more than anything, more than life itself, hanging in the balance, unbeknownst to him.

“I take silence to mean that you’ve accepted your fate, once and for all,” spoke a cold voice, interrupting her thoughts.

Ruby hung up. It wasn’t like she needed to give a response.

Her eyes wandered to the reflection staring, blank faced, at her. Her heart wasn’t pounding, it was near dead. The way she studied her own image with disgust made her think somewhat randomly of Mulan, oddly enough, in the polar opposite of the situation she found herself in. Mulan was the hero, who used a false identity for the good of her loved ones. If Ruby was a Disney critter, as Lilith noted while she mocked her, she was a pretty shitty one. It was downright petty of her to loathe her reflection when it was who she truly was in inside. Saving all of China didn’t seem like an achievement in her foreseeable future.

No manipulation or acting would be of any use, none of her usual bank of problem-solving skills would satisfy this one. It was a choice between mental breakdown, and staying sane for 12 more hours. There was no way to spare Sam all of the pain he was going to feel finding out that she had hired Abaddon to kill him, but at least this way it’d be easier for him to put her in the past, to never want to think back to her again. If there’s one thing she couldn’t bear, it was Sam Winchester spending his life in dejection over her.

In a sort of fleeting thought, she hoped Charlie would be ok. Whoever she was. Logic told her it was unlikely she’d come out of this unscathed either, and it was another stab to the heart seeing someone else’s life crumble, all because of her. On the other hand, Lilith didn’t seem all that confident in defeating Charlie, the way she dismissed her tech-savvy savior with such vaguity. Maybe this girl could still be a resource, if she really committed to carving out an escape route.

“Ruby, you ok in there?” Sam asked, not sounding all that concerned, more… impatient. He probably thought the moment she put down the phone he’d be in her pants. Not that she blamed him; after a month away, the proper way to celebrate would most definitely be some wild, carefree sex on whatever surface seemed to say most that this space was theirs. Maybe breaking some belongings while they were at it- just for the thrill of a sense of ownership.

“Fine, Sammy, just primping a bit,” she replied, trying to sound cool and collected, but still flirty. By her standards, she was doing an ok job. She stripped down to her undergarments, placing her clothes on the tile floor, phone rolled up inside her jacket. Her hair was too neat; she ruffled it a bit, and practiced a look she would call the expression of a sultry Victoria’s Secret model- pouty lips, begging to be ravished.

Ruby opened the door and saw Sam’s reaction; instant excitement. She had almost forgotten how much she loved seeing him like that, and naturally her gaze wandered downward, looking for the bulge that would gage his enthusiasm. It was definitely there, only just getting started.

“Well?” she asked coyly, raising an eyebrow. “Are you going to just stand there looking? You know full well, my body is yours, baby,” she continued, taking a step closer to him so her lips were inches from his neck. With that, she made her best effort to sweep her anxieties under the rug, just for now.

“That’s right,” Sam affirmed in an almost hypnotic voice. “All mine.” He ran his muscular hands along her torso, cupping her rear, and looking down at her like a guest at a fancy dinner party, admiring the appetizer with controlled anticipation.

“Mmmmm… so beautiful,” he continued, and scooped her up so that her arms and legs were latched on to him, carefully lowering her onto the carpet, taking his place hovering above her. When he found the perfect spot on her neck, he dove in and sucked, hard, making fists in her hair. He couldn't stand another moment without his mouth against her skin.

Ruby moaned, so hot, so ready for him, but somehow having difficulty fully relaxing.

"Sam, I...  can we just... pause for a moment?"

“Ok.”

He moved to the side so he lay next to her rather than hovering above, and took her hand, focusing his eyes on hers. She had seemed oddly disconnected, like her mind couldn't fully commit to what her body desired.

“Is something wrong?” he asked, sunflower eyes wide and soulful as ever.

“No, no, just…” she responded in a soft, choked-out sort of voice. “I’m so sorry.”

“For what?” he chuckled. “So you’re not in the mood, everyone has those moments. I don’t want you to feel like you owe me anything.”

Ruby felt the first sting that signalled the emergence of tears. She had been moved to tears with joy and sadness alike more times in her two months with Sam than ever in her life. Sometimes it made her feel weak, but his embraces were almost more intimate when intensified by that surge of emotion.

“That’s not it,” she sighed, and sniffled a bit, propping herself up to a relaxed sitting position. “You trust me so completely, Sam, and there’s so much of my past that I’m still sorting out… I want to make sure you don’t feel too attached to me.”

He looked puzzled, and maybe slightly offended, but still intently gazing at Ruby through soft, loving eyes.

“I’m not one to rush into things, but… well, Dean’s always called me an emotional sap, and he’s kinda right,” he began, raising his own body up to sit beside her.

“I don’t know how to put us into words. Ironic I guess, considering I used to write poetry a lot. Just… I’d always second guess myself, cause I knew I was falling for you way faster than anyone should, but... it didn’t really scare me, ya know?”

She nodded, wiping a tear away.

“I knew for sure, after the whole Abaddon ordeal, that I had to be everything for you, if you could forgive me for what I did. The moment we made it to the lobby of your building, I could hardly breathe, I thought that anyone in their right mind would be disgusted with me, terrified.”

“I could never be scared of you, Sam,” Ruby declared softly, but with incredible conviction, as the first tear rolled down her cheek. “You’re the only real thing I have, and I wouldn’t even for a moment judge you for what you did. I owe you my _life_. I’d jump right in front of a train if it were the only way to save you. I’d die a thousand times for you to live.”

She saw his eyes welling up too; this had to be something like the tenth time they'd found themselves all teary and gushing about love, any other sappy subject that went with it. It was like a joke they were both in on. If Dean were here, he’d be bent over the toilet, puking his guts out.

“Take me to bed,” she whispered, and he took her into his arms, bridal style, like they really were sealing some sort of affirmation. Ruby wrapped her arms loosely around his neck and rested her head on his shoulder, loving the smell of him as she always had. Everything about his body was so warm and inviting; she couldn’t imagine any feeling more blissful.

As Sam approached the doorway, he turned his head to look at her, and smiled coyly.

“What do you want to do in bed?”

Ruby ran a delicate hand along the far side of his face. There it was, there was his invitation to shamelessly give in to that unspoken inside joke.

“I want my man to make the sweetest, most passionate, most ridiculously sappy love to me.”

He’d happily oblige. He never felt like it was unmanly to indulge in the stereotypical girl fantasy- after all, sex was sex.

“Should I go grab some rose petals to scatter everywhere?” he teased.

“Shut up,” Ruby replied before capturing his mouth in a kiss she knew she’d remember for the rest of her life. He responded immediately, kissing her even while he carried her, their faces pressed together with each of her hands. Without breaking away, he moved to the foot of the bed and carefully lowered both of them down.

They had to separate for a moment so Sam could undress. Ruby scooted back so she leaned against the stack of pillows cushioning the headboard, and he couldn’t even bear to break eye contact with her. Every way he could think to describe the burning desire of being so close to her, to love her with everything he had, was inadequate. His only thought was the urgency with which he needed to feel her against him, caress every curve of her body, look deep into her chocolate eyes, listen to her breathing as he pushed her closer and closer to the edge….

Sam shed his boxers and took his cock into his hand, momentarily putting himself on display for her. She giggled, and patted the space next to her to invite him back. In a split second, his mouth found its way back to hers, where it belonged. He sensed she didn’t have the patience for drawn-out foreplay by her frantic fingers clawing at his back, long fingernails marking its muscle-sculpted contours. The slight pain made him feel so alive.

His hand reached down to caress her inner thigh, parting her legs slightly so he could explore the warmth of her core. The thin, smooth silk of her soaked panties was the only thing separating him from the electric touch of his fingertips and her perfectly soft folds, becoming only hotter and increasingly sensitive as he gently stroked them. Ruby's breath hitched, and she bucked her hips slightly when his index finger found her button, not even thinking about it.

"There it is," he said with the volume of a whisper, and yet, a clear, immense pride in his fine-tuned expertise. She moaned, unable to find words to express the mix of ecstasy and annoyance that he got off so much on reminding her of his power over her body, they way she so easily surrendered when he was close. But Sam wouldn’t give her too much teasing down there; the urgency to get to actually making love was a mutual sentiment.

Ruby parted their lips once again, moving her hands behind her back to fumble hurriedly with the hooks holding her bra to her chest, while he took the opportunity to pull her underwear off. Once her breasts were free, he lowered himself onto her again, and took one into his hungry mouth. The flesh was so perfectly soft against his tongue, but her nipple quickly grew into a pebble with a graze of his teeth. Their hips grinded together, his rigid cock sliding along her folds, against the growing wetness of her juices and his precum.

“Enough… Sam, please… I need you inside,” she moaned impatiently, through panting breaths.

It was all the invitation he needed.

He pulled her legs to hook around his waist as he slowly pushed in, not stopping until he completely filled her. She gasped, eliciting a drawn out “yes…” that was barely audible. Still, she didn’t need to utter a word for him to know she loved the feeling of his length fully inside her, nearly pushing her cervix; he was smug, he knew her too well.

The drawn-out moment gave way to smooth, rhythmic thrusts, Sam pushing in and out, kissing her with a softness he hadn’t expected to desire. Ruby wanted shameless love-making, and it was his duty to give her just that.

“You feel so good baby,” he said with his lips hovering above hers, in between passionate kisses. “I could do this forever.”

“Me too.”

Ruby couldn’t believe she had the insensitivity to tell him that, but it was so true, it was truer than anything, the feeling that nothing could ever come close to the bliss of that singular moment.

Naturally, his speed steadily increased, and with her legs still wrapped around him, he grasped her hips for leverage. Again and again he guided his cock as deep as it could go, each time feeling better than the last. He wondered how long is had been… 3, 4 minutes? He couldn’t let himself cum too soon, but it took every fiber of his being to hold off. His body begged him to give in to release, more and more as time went on.

“You close baby?” he asked, feeling it was necessary.

“Mhmm… just... touch me,” she replied, and she guided his arm in between their bodies till he found her clit, and began to make vicious circles against her most sensitive part. It took mere seconds for her to come, her orgasm hitting her out of nowhere like a tsunami against the shore. She couldn’t suppress the cry of ecstasy that escaped her mouth.

Sam realized he might be able to keep going at least another minute, and he’d sure as hell make it count.

Before she knew it, Ruby was coming again, her inner walls clenching against his cock. It was too much, and he gave in to the euphoria of climax just moments after hers began to subside. He gripped her body tightly as he pulsed and released inside her, not letting go till he knew he was spent. Her fingers wove into his hair, and kissed him deeply, desperate to hold on to the moment, letting him go soft still buried in her.

“I love you so fucking much,” she whispered, lost the golden petals of his irises. “Never forget it,” she added, because a stupid little piece of her still clung for dear life to the hope that he wouldn’t forget her, even after she was long gone. That he’d believe she’d been telling the truth.

“Why the hell would I?” Sam chuckled softly. She shrugged in response.

“Well then, just in case I suffer some sort of head injury tomorrow and forget who you are, I’d like you to never forget how fucking much I love you.” He placed the gentlest of kisses on the tip of her nose. “And that I always will.”

Ruby nodded, holding back the urge to burst into sobs all of again. Sam was beyond saving. He’d hate her forever; he’d hate her with ten times the passion of love he felt for her now.

But she promised him she’d never forget, and she damn well wouldn’t. She’d take a piece of him with her forever.

 


	11. Translation

**Notes for the Chapter:**

> Oh my gosh, it’s been… forever! I’ve had a crazy past 8 months and spent 3 of them with no internet access anyway. Also I had a severe case of writer’s block, but once I got past it, oh man, I typed faster than ever before! Inspiration is a crazy, unpredictable thing.  
> I appreciate so much y’all being patient with me and I hope you enjoy this (really fuckin angsty) chapter. I know I said this would be really intense but this stuff took up more than I had previously anticipated, so I promise, the reeeeal intense stuff will be the next chapter.  
> Love you guys <3  
> Dana

She hadn’t bothered to set an alarm clock. Ruby knew she wouldn’t sleep a wink.

It was arguably cruel to keep Sam from sleeping, but they just couldn’t stop, then tumbling beside each other, exhausted, only to get excited all over again. It was as if, on some subconscious level, he knew that it was their last night together. Just the thought of his calloused hands caressing every inch of her body, lips kissing her so fiercely her very breath was stolen, and the indescribable feeling that surged through her every time they came together, how her core pulsed around him while his warm release pulsed inside her-

She suddenly brought her awareness back to the present. Her mind was wandering, trying to think of anything but her imminent surrender, _anything._ By the dim light of the waxing crescent moon, she could make out the peacefully sleeping man beside her, on his back, chest half covered by the disheveled sheets. It rose and fell gently in a slow, mesmerizing rhythm. His head lay to the side on his pillow, facing her, lips gently parted as was characteristic of him. Ruby wondered if he was dreaming, and of what, hoping it wasn't anything about a future with her.

Leaving in the dead of night felt almost unnecessary. Undoubtedly cliche. If Sam was going to find out everything eventually, it wasn’t like protecting him from knowing her side of things was necessary. Did she really have to leave him with no explanation or apology from her, the way she had planned all along? Risky as it was, she desperately wanted to trust Sam loved her enough that if she were to explain the entire plot, and be as cautious as she could possibly be… he couldn’t save her, there was no way, and maybe he’d want to try, but she wouldn’t dare let him. Ruby had one resource left, and her mysterious, Potterheaded ally could be anywhere, her safety not guaranteed.

Logically though, Lilith was most likely bluffing saying she had people to track down Charlie. With Ruby convicted of dozens of crimes she did and didn’t commit, Charlie coming forward with her confessions of hacking the prosecutor would be dangerous for everyone involved.

If only there were some secret language she could speak only to him, Lilith couldn’t know. She spoke 13, 14 if morse code counted. Sam was decent in Spanish, but so was a good chunk of the world. What could they possibly share that Lilith couldn't decode?

Ruby’s eyes wandered the room mindlessly, glancing across insignificant material objects that would live on as mementos. She saw one of her favorite bras lying on the floor at the other side of the room- it had to have been there a month or so. There was no sense in moving it. Sam would surely have no use for the garment, but a piece of her felt like it belonged there.

A stack of DVDs had her suddenly smiling with childish hope, thinking, _eureka!_ It was a shot in the dark, but instantly it occurred to her, a way to tell him everything. Maybe Lilith watched Game of Thrones, but the odds of her being fluent in Dothraki of all things were slimmer than her waist in a pencil skirt.

Ruby carefully slipped out of bed, naked and a bit cold, but not caring in the slightest. She grabbed a pen she saw on Sam's nightstand, and the pad of paper next to it, as well as his phone. Lilith was most definitely tracking her phone in some way, and maybe his too, but there was a pretty good chance she was too lazy to pay much attention to his incognito browser searches as 4 AM. After all, she would have an extra early start to her morning.

The device vibrated when she disconnected it from the charger, startling Ruby a bit; she flashed around to look at Sam, praying he wouldn't stir.

His arm moved slightly, the one that lay alone on her side of the bed, and maybe the sensation itself wouldn't have woken him, but his body just knew somehow that it wasn't wrapped around someone, as it had been mere minutes ago. He mumbled incoherently, concern evident in his tone. She could make out something that sounded like, "Come back..." and it shattered whatever last piece of her heart wasn't already in pieces.

Her will to resist his sleepy beckoning was fading. It took everything she had to keep it alive, and the best way to do that was to bring her focus back to the task at hand.

She tapped on the empty box where the original text went, and began scribbling her final  to the love of her life.

...

Lilith started her morning with a swig of her favorite liquor. She couldn't care less how her therapist would shudder if he knew how her drinking habits were getting this pitiful, relying on toxins to keep herself sane at 4 AM. Nothing soothed her like the sweet, burning sensation that she could feel travel down her throat, pump into her veins. How it brought both numbness and excitement to every inch of her body.

Truth be told, Ruby was getting to her- and that was a huge understatement, but she simply couldn't allow herself to admit to experiencing anything more than mild intimidation. The more her anxiety grew, the more she revelled in an almost psychopathic fantasy of every brutal, depraved, horrific way she could torture the little slut. Not Lilith personally, of course- she had employed some help from friends for that task.

A knock on her door caught her by surprise, even though she was, in a general sense, expecting it. It did alert her to the fact that she had somehow wound up slumped against the wall, her bottle held loosely in her hand, limp and tipped to the side. Luckily, not too much of her precious poison had spilled out.

She gathered herself as quickly as she could, smoothing out the dress she had put on for work the previous morning, which she still wore. There was no use in trying to fool this serial killer Metatron that she was as put-together as she made herself out to be, but it wasn't as if his opinion mattered.

Lilith opened her door and was relieved to be in the collected presence of her assistant, Alastair.

"He's in the car," the man stated simply. He was well-dressed as usual, hands clasped in front of him.

“Ok, just-” Lilith exhaled tensely, running a hand through her mangled blonde hair. “Um, give me a sec to get dressed.”

She didn’t wait for a response before making her way to her room and grabbing the first things she saw- a cream-colored blouse and navy blue skirt, with matte black leather heels. Her make up was good enough as it was, and she could just put her hair in a quick french twist to make it presentable. On second thought, she traded her cream top for a black one- easier to clean up if any blood got on it.

When she came back to the door, Alistair was gone.

She made her way to the elevator, strutting as if the empty, carpeted hallway were a catwalk; for her own sake, she needed to feel confident, self-assured. The particularities of this operation would be handled by someone else, a real professional in that field. As much as she craved revenge, Lilith still needed to maintain her sanity, keep herself grounded. This was ultimately for an important cause, at the end of the day, and that's what mattered. If she weren't so uneasy, she'd be giddy to see the look on Lucifer's face when he saw all that she had accomplished.

Her ride was parked as close to the exit of her building as it could be. Lilith stepped into the black SUV, and closed her stinging eyes with a drawn out sigh.

"Even more delectable in person," remarked a high male voice, each word dripping with snark.

She lay her eyes, for the first time, on Metatron. He exhibited the proudest smirk a man in his situation could. It could very well be the best day of his Goddamn life, and getting to ditch the unflattering orange jumpsuit for actual clothes was only the beginning.

As the vehicle began to move, Lilith smiled curtly at the man beside her, ignoring his vaguely threatening compliment.

"I suppose formalities are unnecessary Mr. Metatron, and time is of the essence, so let's go over the agenda."

"I couldn't agree more, Ms. Carter," he responded smugly.

"Let me preface our discussion with a reminder that I have employed your assistance for one reason, and one reason only. Do I have your word that you will not use your furlough as an opportunity to do anything but what you are told?"

"Wouldn't dream of it."

The ride seemed to last for ages, and it was only 15 minutes. Lilith scrolled through her facebook newsfeed nervously, liking her friends’ pictures of their babies and People articles about the latest celebrity scandals- Disney star Krissy Chambers just got caught smoking pot, that gave her a good chuckle. She was vaguely aware of Metatron twiddling his thumbs and humming that Alanis Morisette song, his simple manner making him come across as either completely sane or insane beyond all reason. Either way, she was sure she had picked the right guy for this job.

As the SUV pulled into the parking lot, illuminated only by dim, yellow-tinted light, she shuffled in her seat, and gave Metatron a nod signalling they should prepare for Ruby’s arrival. It took a bit of searching to find her, but after scanning the lot with scrutiny, Lilith found her nemesis leaning casually against a wall next on the bottom floor. Her arms were crossed, and she would have seemed collected if her face wasn’t so somber, staring at the floor with an expression like she wished she could cease to exist.

Lilith grinned; if she wasn’t dead inside, she sure would be pretty soon. Literally.

“Found her. Wall next to the elevator on the right.”

Alistair turned the wheel and drove slowly in Ruby’s direction, til he reached her at last. Lilith rolled down her window, smiling with sadistic glee as she looked her up and down. It was as if the woman before her was her own personal masterpiece, a victory, crushing the tragic Romeo and Juliet fantasy of her traitor. She could hardly wait to see Ruby covered in blood, clothes ripped to shreds, screaming for mercy.

“You look well,” she remarked snidely.

Ruby gave no response, clearly beyond the point of caring to defend herself against Lilith’s taunts.

“Hop in,” she continued, and raised a manilla file fat with papers so Ruby could see it, pretending it was the culmination of painstaking research into all the records of her past. In reality, it was a collection of the owner’s manuals to various electronic appliances Lilith owned. “We’ve got the goodies all ready.”

Out of the corner of her eye she saw Metatron reaching for the chloroform soaked rag they had prepared for their guest. The moment Ruby joined them, she’d be receiving a rather unfriendly welcome.

The brunette walked wordlessly towards the SUV, and revealed some papers of her own- Lilith wanted to laugh, the little skank actually prepared documents to bring about her own downfall! It was pitiful, and it only served to remind her she had no reason at all to be intimidated. Ruby was no threat to her, she never was.

She placed on leather boot in the car, and milliseconds later found herself with a violent arm around her waist and a wet rag over her nose and mouth. Her resistance was effortful; she went down kicking and screaming and scratching and Metatron’s arm with her black-polished nails, but within a minute, her whole body was limp in his arms, and her papers slid from her hand.

Ruby was tossed carelessly onto the floor, landing on her back with her head tipped to the side, dark brown hair fanned out around her. Lilith saw the stains of black mascara that lined her cheeks, and cackled, vividly imagining her helplessly crying for her precious Sammy as she awaited her fate.

Lilith rolled up the tinted window and sighed with satisfaction. Metatron’s eyes lit up with excitement as he eyed his captive.

“Can’t wait to play with this one,” he chuckled, and grabbed her by the arm. He began unzipping her jacket with his other hand, but Lilith brushed it away.

“Ah ah, patience. There’ll be plenty of time for that later.”

Metatron released her, not terribly disappointed.

“Fair enough. I do like ‘em feisty, watching ‘em break down til all that feist is gone.”

Lilith smiled.

“I knew I chose you wisely,” she sighed, and her eyes shifted to the floor, where Ruby’s papers fell. “Wonder what kinda shit’s in here…”

She wasn’t sure what she had expected to find, but it wasn’t 70-something pages, all identical, mostly blank, only “go fuck yourself” handwritten in the top left corner.

…

Sometime around 9 AM, Sam became vaguely aware of the emptiness next to him. He rolled over, half-awake, and expecting his arm to land on a warm body, but it fell to the sheets. It was easy to assume Ruby must’ve been in the bathroom, but the uneasy feeling in his gut told him otherwise. The surface was cool. He’d been alone for at least an hour.

He propped himself up, yawned, stretched his arms, realized he should probably go take a shower. Yet the need to know where Ruby had gone was at the forefront of his mind.

Sam’s phone buzzed, and he turned to see that it was charging. He didn’t remember plugging it in last night, but then again, he was thoroughly distracted. He leapt up awkwardly to grab it, naturally hoping it was her.

It was Jo.

_Dude, congrats! You gonna show me what it looks like?_

Sam was only somewhat disappointed; it wasn’t Ruby, but at least it was an opportunity to talk about Ruby. He placed his phone beside him and rolled over so he could gain access to the drawer on his bedside table, digging through various small items til he found the box his phone came in. He opened it, revealing the cleverly hidden dark red, velvet box, and inside that, a diamond ring.

He snapped a picture and sent it to Jo, then turned off his phone, figuring she wouldn’t kill him if he resumed the conversation later.

Ruby was the only thing on his mind, and it had been since they met. He had gone and bought the ring on his own a week ago on something of a gut feeling- they hadn’t known each other all that long, but if Sam was one thing, it was a hopeless romantic. The ring was simple; Ruby wouldn’t wear anything too gaudy. Just a gold band engraved to look like there were two strings wrapped around each other with the perfectly polished gem melded in.

Carefully, he put his secret away, exactly where it was before. And that was when he noticed a handwritten note on the bedside table.

Ruby’s handwriting.

He picked it up and began to read.

_Sam, anna athfiezar…_

“What the..?” he muttered to himself, scanning the page for something that resembled English. He was no language expert, but whatever this was, he had never encountered anything like it before. The only part he could read, other than his name, was the very last sentence: _In the tongue of the dragon queen._

Clearly it was a clue as to what language this was; context told him “tongue” was not referring to the body part. What puzzled him was not the language itself, but why she insisted on being so cryptic. Was it a treasure hunt or something?

He sat back onto the bed, staring at the ceiling, pondering all of this. The dragon queen… why did he feel like he knew what that meant when he couldn’t quite put his finger on it?

His eyes scanned the room aimlessly and landed on a stack of DVDs. It struck him immediately; of course! Daenerys was the dragon queen, so this language was either Valyrian or Dothraki. It wouldn’t surprise him if Ruby spoke one of those fluently, but more likely than not, there was a translator out there, somewhere in the niche of the internet where people have nothing better to do than dedicate themselves to constructing translators for made up languages.

Sam grabbed and turned on his phone and, more quickly than he expected, found what he needed; he decided to try out Dothraki first and try Valyrian if that didn’t work. He began frantically typing in the words, his heart pounding for some reason he didn’t quite understand. All he knew was his intuition told him this was either a very good thing or very, very bad.

When he was done, he hit submit, and it worked.

He took a deep breath, and read.

_Sam, my love:_

_I know this is the absolute worst way to have to tell you this, but I can’t do it in person, I just can’t._

Oh God, Sam thought. This can’t be happening.

_There are a lot more secrets of my past I never told you. Things you deserved to know long ago. Maybe even the moment you met me. For almost the past decade, I’ve been for hire to assassinate people or hold them ransom, that’s how I got so rich. At first it was the only way I could make money without sacrificing my dignity. And my most recent assignment was… well, you. We met at that bar because I very intentionally planned it that way. Or rather, Lilith Carter, Mark Lucifer’s assistant did._

_Remember when I dropped that water glass? It had a roofie in it. No, I wasn’t going to date rape you, just knock you out so I could turn you in and let Lucifer handle the rest, hold you ransom so your father would withdraw from the election and effectively hand the primaries to Lucifer._

_You don’t have to believe me on this, and to be honest, no self-respecting person should, but I will never forgive myself if I don’t say it. I love you. I love you more than I thought I was even capable of loving anyone. The moment I met you I knew I would never be able to go through with it._

_Abaddon wasn’t trying to mug us. She was trying to kill me. Lilith hired her to because I quit the job; I no longer had any desire to hurt you or your family. Not for a million dollars. You went through unimaginable trauma all because of me, and I’m so, so sorry, if sorry even means anything now._

_All I ask of you now is one thing; be happy. Live your life. Find someone who can really love you, dedicate themselves to you, give you what you deserve. If you hate law school, fuck it. If you think it’s still worth pursuing, give it your all. Forget me. If you feel any shred of love for me, you can do me this much._

_Please don’t go looking for me. It’s not worth it._

_Yours truly,_

_Ruby_

Sam hadn’t noticed his eyes welling up, but at some point reading this, they had. Stupid Ruby, always turning him into a sap. And yet, he wasn’t sad so much as just… everyone possible negative emotion, all at once. Of course he was furious, betrayed, wondering if these last few whirlwind months were all a lie. But why would Ruby go to all this trouble or staying with him and giving a damn convincing performance that she loved him if she still wanted to hurt him? What made him feel shittiest of all was the fact that even after this revelation, he still couldn’t hate her. All he wanted to do was rummage his cabinets for the strongest drink he could find, consume it til he blacked out, and maybe just die if he was really lucky.

Sam’s thoughts were terrifying him. She thought he could just move on so easily, as if this relationship was nothing to him. Clearly she had no idea that hidden away was a little velvet box intended for her. For them.

Just then, his phone interrupted his thoughts. The fucking Game of Thrones theme, the last thing on earth he wanted to hear right now. He reached over to put it on silent, but some stupid part of him wondered if it was Ruby. Maybe, just maybe, she’d changed her mind. It was from a private number but Ruby probably knew how to use those.

“Hello?” he answered, trying to sound stable.

“Sammy. Nice to finally speak to you.”

The cool female voice sent an immediate wave of unease through him.

“Who-”

She interrupted him, chuckling darkly.

“That doesn’t really matter. I just thought I should let you know that we have someone we think you might like to see. I’d let you chat with her now but- well, she’s detained at the moment.”

“Ruby…” he whispered, feeling his chest suddenly collapse.

“Ding ding ding!” the woman responded mockingly. “You have til 1 PM to arrive at 1983 Lawrence St., in Fair Haven. Cute little town, lots of space for abandoned warehouses. And if you decline the invitation, your sweetheart will suffer torture like you couldn’t even dream of, and I’d hope you’d be willing to clear out your schedule for today to prevent that. See you soon!”

The moment she hung up, he threw his phone at the wall, his body shaking, heaving, unable to cry or scream or do anything either than descend into shock.

But he had no choice, that was made abundantly clear. He picked up his luckily undamaged phone from the ground, grabbed his keys, and muttered, “I’m coming,” hoping wherever Ruby was, she knew he would never abandon her, no matter what.

**Notes for the Chapter:**

> Yes, Dothraki translators do in fact exist, but there aren't actually a lot of words in them. At first I tried to translate the entire note but I couldn't, so just... extend your imagination here! It's way less crazy than a man named Lucifer running for president, right?


	12. The Villain Monologues

**Notes for the Chapter:**

> READER DISCRETION IS ADVISED! This chapter contains potentially triggering descriptions violence, verbal taunting, torture, attempted sexual assault, and corpses. (Not to spoil anything... but my readers' comfort and safety is far more important than keeping my plot secret.)
> 
> IF YOU CHOOSE TO NOT READ, A TRIGGER-FREE SUMMARY CAN BE FOUND AT THE END. Click on the shortcut to notes at the bottom (or just scroll down reeeeally fast xD)

Ruby’s eyes slowly opened, though they were impossibly heavy. She almost wished she’d kept them closed when the first thing she saw was a certain blonde bimbo looking more deranged and psychopathic than ever.

It was instantly clear she had a cloth gagging her, and it took another four milliseconds to gather she was bound by plastic zip ties to a chair. She couldn’t help but chuckle; if only she had a nickle for every time she had been in a situation like this, and every time she managed to escape…

“Surprise!” Lilith cackled. “You really didn’t think I’d let you off that easy, did you?”

Truth be told, of course Ruby didn’t, she wasn’t stupid. It was always a possibility Lilith had been lying. She just didn’t care. A piece of her felt that whatever happened to her in the end, she deserved it all, and more. All that mattered was that Sam was safe.

“I brought someone for you to meet… maybe you know each other? Friend of a friend? He seems to know a fair amount about you,” Lilith continued, gesturing to a grizzly man in the corner, leaning casually against the wall with his hands crossed, grinning like the Cheshire cat.

“Ah, Ruby,” he sighed in his unnervingly high-pitched voice, moving slowly towards her. “So nice to finally meet you. Metatron, by the way,” he said, extending his hand for her to shake. “Oh, sorry, I forgot,” he chuckled, mocking her incapacity to move her arm. “Maybe you’ve heard of me? I know for a fact you were acquainted with my old friend, Gadreel.”

Ruby hadn’t heard the name in at least five years, maybe six…. Gadreel, the mobster she poisoned while he took her on a fancy date. Of course she knew who Metatron was; deranged serial killer, responsible for the murder of something like 18 people, mostly hookers and rival mafia members. And yet his sleazy lawyers got him off with only two convictions and a lifetime sentence. It was all over the news several years ago. But she had no idea he was connected Gadreel!

Unable to speak, she just rolled her eyes.

“Lucky for you, the fun won’t start til your boyfriend arrives, Lilith began. “Assuming he does, of course.”

They were going to torture her. Of course they were. She had weaseled her way out of situations like these too many times to count, but she had gotten so good at avoiding them, she wasn’t sure if she could this time around. Not with Sam’s safety at stake. A surge of terror struck her whole body; all of this was to avoid putting him in danger! She couldn’t care less about her own life at this point, as much as it pained her to admit to herself. And she could endure a lot if it meant saving the only precious thing she had anymore. What did they even want from him? Were they going to torture him too?

“I’m sure you’re wondering what this ‘fun’ entails, and considering we don’t plan on you being around to see it all, I figure it’s only polite to tell you.”

God, Lilith again with professing her evil scheme to her still-breathing victim. How dumb was she?

“Metatron has lots of plans for you. Best part is, all Sammy has to do is watch, and hopefully that’ll give him enough of a shock to make him a convincing psycho,” Lilith chuckled darkly. “No one will believe him if he says he didn’t rape, torture, and kill you when he was the only one of the scene, and, well, more than capable of doing those things. It will blow up in the tabloids, and instantly ruin his father’s career. Would you vote for a man whose son would do all that crazy shit? Yeah, me either.”

Ruby had never felt more empty, more pitiful, more hopeless in her life. It was almost a Godsend when a fist to her skull caused her world to go dark instantly.

…

Sam was sure he’d exceeded his maximum heart rate as his car stopped for the first time in at least 2 hours. How he hadn’t crashed into someone or something was a mystery. All he could think about was all these conflicting emotions towards Ruby… how he knew he should hate her, but he couldn’t, and how scared he was, and how she didn’t deserve any of this, or maybe she did… either way, he wouldn’t stand idly by while God-knows-what happened to her. No one deserved to be tortured.

The warehouse was much nicer than the rundown, crumbling building he had pictured. It was painted a deep red, chipping a bit, but otherwise looked like with a sign and some windows, it could easily be a business.

Unsurprisingly, the door was locked. Sam pounded his fists against the wood, adrenaline preventing him from even feeling the pain in his knuckles.

It occurred to him too late that he should’ve checked his surroundings before so boldly announcing his arrival, because before he knew it, he was grabbed from behind. He squirmed to try to break free, but a second body forced his head into a dark sack, disorienting him and robbing him of his vision. Sam kicked his leg out and managed to knock down whoever blinded him; the attacker let out a shrill yelp, indicating it was a woman, the same woman who had called him. Lilith Carter, he presumed. Her accomplice he was unable to shake. His arms were thrust behind his back, and he suddenly felt strong plastic pressing into his skin, binding him.

“Son of a bitch…” muttered the woman, her voice traveling upward as she lifted herself from the ground. “Throw him inside,” she ordered, and in an instant, he was pushed forward to land on hard concrete. The door closed behind him with a thud.

“Check him,” Lilith instructed in a cooler tone, more relaxed now that she had regained control. Sam felt aggressive hands pat their way up and down his body, and he held his breath, praying they wouldn’t happen upon the handgun he’d stashed away in his jacket.

“Wow, never woulda guessed pretty boy here knew his way around firearms!”

Fuck.

The man removed the gun and, Sam assumed, stuck it in his own pocket.

“Don’t worry Sammy,” Lilith mockingly assured him. “We’ll take the sack off once you’re seated comfortably. You’ll get a front row seat for all the action!”

His captor pulled him roughly forward, and Sam didn’t fight, knowing it was the only way he’d get his vision back and be able to assess the situation. He’d had a fair amount of training in self-defense, given how his father’s position of power might put him at risk for something like this happening. He just never imagined it would, or that he would walk into it so recklessly, so unprepared, not like his usual cautious self at all. But he did have a nasty habit of letting powerful emotions eclipse all else.

When he was secured to what felt like a wooden post, the man did as Lilith said he would and pulled off his blindfold.

Immediately his eyes were drawn to the unconscious woman gagged with a cloth and bound to a chair, her body limp, head fallen forward, her messy brown hair covering her face.

“You bastards!” Sam grunted, instantly overcome by fury. Ruby was so strong, so confident and powerful, what did they do to her to capture her like this? What worried him more was what they were planning to do to her once he got here. He had a feeling he didn’t want to even find out.

Lilith chuckled, crossing her arms in front of her chest. Truth be told, she was an attractive woman, with blonde hair and an hourglass figure, but her facial expression conveyed clearly that what went on inside her head that led her to commit such a crime and take pleasure in it was anything but charming.

“Oh Sam, don’t tell me you aren’t at least a bit happy to see her like this. The little bitch was supposed to kidnap you and ruin your family, was she really such a good fuck the truth about her doesn't bother you?"

Sam said nothing, just sat there with his heart pounding, his nostrils flared, breathing heavily.

"You overestimate him, Lily," sighed the man. Sam realized he hadn't actually gotten a good look at him; he was short with curly salt and pepper hair, wearing a casual sweater. He strolled over to Ruby, admiring her as if she were a doll on a shelf, and reached out to tuck a string of her hair behind her ear.

"Let's find out just how good a fuck she is."

Blood burned hot in Sam's veins, adrenaline surging through him. If he even tried to hurt Ruby, he was a dead man the moment Sam could free himself, and he intended to.

"Wakey wakey," the man said, tapping on her temple. When she didn't respond, he smacked her straight across her face. That did the trick. Ruby made a muffled noise that could've been a cry or a whimper, and her eyes shot open.

"Ruby!" Sam yelled, for no reason other than to let her know he was there, he hadn't abandoned her.

"Sam!" she screamed, and even with the cloth in her mouth, he could tell what she said.

"This lovey dovey vibe I'm getting is going to make me throw up," Lilith commented nonchalantly. "Metatron, can we get to it already?"

Metatron's slowly lips curled into a twisted, disturbed grin.

"My pleasure."

With that, he whipped out a pocket knife, and took his time considering his options.

"Handy little tools, these are," he mused. "So underrated, for all their uses in torture. Like, this, for example.”

Ruby made no sound as he slashed right through her shirt, just winced, though Sam could tell she was terrified. She always needed to be strong, he knew that about her. She wouldn't go down without a fight.

Suddenly, he had an idea.

He waited until both Lilith and Metatron were focused on Ruby to start squirming his lower body, trying to push his key out of his pocket. If he could get it on the ground, rotate himself just enough so he could grab it, and slowly cut away at the hard plastic tie binding him, maybe he could manage to escape. Other than try to be as sly as possible, all he could do to help himself was pray Ruby could fight back and stall long enough so he could break free.

Now that the only thing covering her chest was her bra, Metatron had lots of skin to work with. He began slicing away at random spots, eliciting only tiny whimpers from his captive, not even pausing until most of her upper body was dripping with bright red blood.

"She's given up!" Metatron exclaimed, looking towards Lilith. "What happened to my feisty little girl? I was so looking forward to beating that feist right out of her," he said, addressing Ruby. She stared fiercely into his eyes, warning him with no words that he shouldn't jump to conclusions.

Logistically speaking, he'd have to cut her legs free at some point. Her body was going into panic mode, knowing he was going to try to rape her, but at least she could use it against him, and prevent him from succeeding. Her brain was working a mile a minute, thinking everything through, every move she would make and the responses she anticipated. It was the only thing to distract her from the pain searing across her body and the knowledge that she had, for the second time, put Sam in danger. If she didn't stop Metatron and Lilith, she'd be dead, Sam would spend at least a lifetime in prison, and Lucifer would win, the primaries at least, though she didn’t really care much for politics anyway.

She knew she was reaching the limits of her endurance when he drove his knife right into her leg, withdrawing it quickly and admiring the dark red spot that appeared and rapidly grew. She was breaking, letting out her first real cry since he slapped her into consciousness.

"That gag must be getting frustrating, huh?" Metatron stepped back, obviously giving her time to really experience the agony. "Tell you what, I'll pull it off if you suck me cock, and promise to be a real good girl."

Of course he was lying, he knew Ruby would never say yes, and even if she did, it would only be to try to bite him. Once again, she just stared back, that same vicious glare she had given him earlier.

"Oh well, if that's how it's gonna be, I'll play ball."

In her peripheral vision, she could see Sam wiggling in some oddly intentional way... he was going to break free, he was clever, but she knew he'd pay dearly if he failed. Her eyes darted to him, sending a wordless message- Please be careful.

He responded- It’ll be ok.

"Look at me, you little whore!" her captor growled, jamming the knife into Ruby's other leg with at least twice as much force as he had before. Ruby screamed, tears streaming down her cheeks as he twisted it, cackling. Sam stopped dead, his eyes wide in panic.

"Sammy can't save you now, sweetheart," Metatron said, regaining calmness, and clearly heading towards what he'd been threatening for a while. His eyes lit up with maniacal glee as he traced the knife down her aching legs, clearly assuming he'd severed enough nerves to make it hard for her to kick him once he cut her legs free.

"Lily!" he called out. "Why don't we give Ruby here some incentive to cooperate? She wouldn't try to stop me if it meant watching Sammy's brains get blown out, would she?"

Lilith smiled, walking towards him as if she were in a professional setting, heels clicking.

"I agree."

Metatron grinned, handing her the very gun he had confiscated from Sam. She pointed it directly at him while she walked to where he was tied up, her facial expression telling him she wouldn't hesitate to pull the trigger.

But Ruby knew better. If Lilith lost Sam, she'd lose her only major advantage in the plan to force John to resign. On the other hand, she had proven herself adaptable, and maybe a dead Sam could be just as useful as a living one.

"Now, where were we?" Metatron said, pulling a little aluminum package from his pocket, and tossed it onto her lap. “Don’t think I’m stupid enough to leave DNA evidence. Now that would just be un-gentlemanly.”

Ruby’s heart pumped even faster as she understood his words; men had threatened, but she’d always prevented it with relative ease, never had it come this close….

Metatron bent down, his knife ready to cut. In a fraction of a second that seemed to last hours, Ruby made up her mind. The room was so silent she could hear the swish of the blade as it cut through the tie.

Her heart pounded, but she stayed still as a statue.

"Good girl," he remarked, moving to cut the other tie, the last barrier preventing him from ripping her clothes off.

The moment his eyes focused on her other ankle, Ruby quickly threw all of her weight into her free leg and swung her body around with the chair. Metatron howled as he was knocked over by the force, causing his knife to slice right through his eye. Ruby hadn't planned that part, but her quick, resourceful self-defense move couldn't have gone better.

And within milliseconds, Sam busted out of his captivity, tackling Lilith and ripping the gun from her hands. Shots sounded, echoing powerfully through the room as Metatron crumbled to the ground, nearly every major organ gushing blood, and a shot to the head had killed him instantly. Next he had to handle the screaming, wildly kicking woman he held down with his foot. Having strong legs was rarely a disadvantage.

“Please!” she cried, begging. “Please, I was never going to kill you, I just… you know Ruby has killed people, right? Am I really so bad?”

Sam considered it for a moment. But his purpose was clear; of course he’d had to save Ruby from being tortured, raped, and suffering a brutal death. No one in the world deserved an experience that horrific. Still, he wasn’t so sure about their relationship.

He turned to look at Lilith, chuckling.

“Yeah, I think so.”

And with that, he shot her in the leg. She howled in agony.

“I’m not gonna kill you, not now. I want to see the whole world find out what you did. So consider this a warning.”

As soon as Sam was sure Lilith was rendered helpless, he directed his attention to Ruby. She lay on the concrete floor, covered in blood, still mostly attached to the chair. But she was safe now, everything would be ok.

He rushed over to her, falling to his knees to untie her, and remove her gag.

“Gross,” she commented, wiping the saliva coating lower half of her face with the back of her hand.

“I’m so sorry, Ruby, I-”

“Not even remotely your fault. Any of this.”

Sam gazed back at her, eyes swimming with a trillion emotions. The only action that made any sense for him was to pull her forward, press his lips to hers, and kiss her til his body knew she was there, safe, and this nightmare was over. It was wrong, confusing, but deep down he knew nothing else mattered, just Ruby, just his love.

When he felt a cool sensation against his chest, he was reminded that she was still bleeding, everywhere. He had stashed his phone in his underwear;awkward as it was, it was the hiding spot with the least chance of being found. He would’ve put his gun there, but… accidentally shooting himself in that area would be pretty damn unpleasant.

“911, what’s your emergency?” a cool male voice asked, as he was trained to.

“Yeah, um… there are two people severely injured here, and one dead, after a hostage situation… please just send someone, I don’t know how to explain everything over the phone.”

“They’re on their way. Do you suspect that wounds could be fatal?”

“No, one person is shot in the leg, one of the kidnappers. And with the victim, there’s a lot of blood… stabbings. I should just apply pressure, right?”

“If it's safe, you’re going to have to remove or rip open any clothing covering the-”

A gunshot sounded, followed by a female scream.

“Sir? Sir, is there currently gunfire?”

Sam collapsed to the ground as the phone fell from his hand. Ruby saw gushing red on his chest, so close to his heart… no, he couldn’t have been shot there, he couldn’t die like this…

She whipped her head around to see Lilith crawling desperately towards them, her leg dragging and creating a bloody stripe across the floor. In her hand was a small pistol she had likely brought herself.

“You… You…” Ruby growled, her voice’s volume rising. Truth be told, she had no words for this insane, awful, twist excuse for a human being, and nothing was stopping her from blasting her brains out with Sam’s gun.

“Go to hell.”

She shot. Again and again and again, til there were no bullets left.

Lilith was a pretty horrific sight to behold, head mutilating, literally revealing some grey matter. As disgusting as it was, it wasn’t even close to how disgusting this woman had been. She’ve loved to do that to every single inch of her body, but there were more pressing matters.

Ruby turned away, not caring much to see any more of the mangled body of the woman who murdered the love of her life.

Collapsing to her knees, her face in her palms and tears streaming down, she wondered if she could even live another day. As she moved her hands down, she found herself looking at Sam… his eyes closed, blood spilling everywhere, his chest slowly rising and falling….

Her eyes suddenly lit up with hope, and she quickly grabbed his wrist, finding a pulse. She’d thought the bullet reached his heart, but she realized now that it’d just missed it. And if Sam were left there for too long, there was no way he’d make it, but if the paramedics arrived as soon as they were said to arrive, he had a chance.

It hit her with a devastating pang in the chest, knowing that there was no way she could stick around. Sam was better off without her. She’d known for ages but been too selfish to leave him, to let him live his life and find some lovely girl he could really love in a stable relationship, marry, have kids, all the things she could never give him. Of course Sam would be devastated, search for her, but he would get past it eventually. Maybe he already had- maybe he cared about her just enough to want to save her life, but how could she possibly think he would want to stay with her, after all this?

Ruby made her decision. She would stay with him until she heard the sirens coming close. And then, as fast as her bloody, weak legs could will her to, she’d run.

Just as her thoughts were sorted out, the blessed sound she’d longed for filled her ears. With one last longing look at the man lying almost lifelessly on the ground, she made her way towards the exit.

**Notes for the Chapter:**

> Trigger-free summary:  
> Ruby wakes up tied to a chair with Lilith and Metatron eager to torture her. Sam arrives but is captured as well. Metatron reveals he has a grudge against Ruby because he killed his friend, Gadreel. Lilith explains her plan, to frame Sam for Metatron torturing Ruby and sabotage his father's campaign. He begins to torture and and Lilith points a gun at Sam so Ruby won't fight back. Meanwhile, Sam finds a way to slyly free himself using his key to cut the plastic tie holding him.  
> When Metatron tries to cut Ruby's legs free, she whacks him with the chair, giving Sam an opportunity to break free and shoot Lilith in the leg, but spares her life. He shoots Metatron dead though. He frees Ruby and overwhelm with emotion, they kiss. Sam then calls 911. After he talks with a responder a little bit, Lilith shoots him in the chest, and Ruby shoots Lilith multiple times. She thinks Sam is dead, but soon realizes he isn't. As the paramedics arrive, she decides to escape and leave Sam's life.


End file.
